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{{Medical}}
{{Medical}}
{{Drugbox
{{Infobox drug
| Verifiedfields = changed
| Verifiedfields = verified
| Watchedfields = changed
| Watchedfields = verified
| verifiedrevid = 464189683
| verifiedrevid = 464189705
| image = Entecavir structure.svg
| image = Ephedrine.png
| width = 240
| width = 225px
| alt = Chemical structure of the (1''R'',2''S'')-ephedrine molecule
| alt =
| image2 = Entecavir ball-and-stick model.png
| image2 = (1R,2S)-Ephedrine molecule from xtal ball.png
| alt2 =
| width2 = 225px
| alt2 = Ball-and-stick model of the (1''R'',2''S'')-ephedrine molecule
| caption =
| caption = (−)-(1''R'',2''S'')-ephedrine chemical structure (top) and ball-and-stick model (bottom)


<!-- Clinical data -->
<!-- Clinical data -->
| pronounce = {{IPAc-en|ɛ|n|ˈ|t|ɛ|k|ə|v|ɪər}} {{respell|en|TEK|ə|veer}}
| pronounce = {{IPAc-en|audio=En-us-ephedrine.ogg|ᵻ|ˈ|f|ɛ|d|r|ɪ|n}} or {{IPAc-en|ˈ|ɛ|f|ᵻ|d|r|iː|n}}
| tradename = Baraclude及其他
| tradename = Akovaz、Corphedra、Emerphed及其他
| Drugs.com = {{drugs.com|monograph|entecavir}}
| Drugs.com = Ephedrine: {{drugs.com|monograph|ephedrine}}<br />HCl: {{drugs.com|monograph|ephedrine-hydrochloride}}<br />Sulfate: {{drugs.com|monograph|ephedrine-sulfate}}
| MedlinePlus = a605028
| pregnancy_AU = A
| pregnancy_AU_comment =
| DailyMedID = Entecavir
| pregnancy_AU = B3
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Entecavir (Baraclude) Use During Pregnancy | website=Drugs.com | date=2019-12-03 | url=https://www.drugs.com/pregnancy/entecavir.html | access-date= 2021-01-24 | archive-date=2016-11-07| archive-url=https://web.archive.org/web/20161107162421/https://www.drugs.com/pregnancy/entecavir.html | url-status=live }}</ref>
| pregnancy_category=
| pregnancy_category=
| ATC_prefix = C01
| routes_of_administration = [[口服給藥]]
| class =
| ATC_suffix = CA26
| ATC_supplemental = {{ATC|R01|AA03}}, {{ATC|R01|AB05}} (combinations), {{ATC|R03|CA02}}, {{ATC|S01|FB02}}, {{ATCvet|G04|BX90}}
| ATC_prefix = J05
| ATC_suffix = AF10
| ATC_supplemental =

<!-- Legal status -->
| legal_AU = S4
| legal_AU = S4
| legal_AU_comment =
| legal_BR = D1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_CA = Schedule VI
| legal_BR_comment =
| legal_CA = Rx-only
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = POM
| legal_UK = POM
| legal_UK_comment = /{{nbsp}}P<ref>{{cite web | title=Ephedrine Hydrochloride 15mg Tablets Summary of Product Characteristics (SmPC) | website=emc | url=https://www.medicines.org.uk/emc/product/2577/smpc | access-date=8 October 2020}}</ref><ref>{{cite web | title=Ephedrine Nasal Drops 1.0% Summary of Product Characteristics (SmPC) | website=emc | date=11 March 2015 | url=https://www.medicines.org.uk/emc/product/4840/smpc | access-date=2020-10-08 | archive-date=24 October 2020 | archive-url=https://web.archive.org/web/20201024054433/https://www.medicines.org.uk/emc/product/4840/smpc | url-status=dead }}</ref>
| legal_UK_comment =
| legal_US = Rx-only
| legal_US = Rx-only
| legal_US_comment = /{{nbsp}}OTC<ref>{{cite web | title=Akovaz- ephedrine sulfate injection | website=DailyMed | date=16 April 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=25828db2-4942-4f7c-a0d5-dc66f82cfb71 | access-date=8 October 2020}}</ref><ref>{{cite web | url=https://ecfr.federalregister.gov/current/title-21/chapter-I/subchapter-D/part-341/subpart-C/section-341.80 | title=Title 21: Food And Drugs Part 341—Cold, Cough, Allergy, Bronchodilator, And Antiasthmatic Drug Products For Over-The-Counter Human Use | website=Electronic Code of Federal Regulations | access-date=2020-10-08}}</ref>
| legal_US_comment = <ref name="Baraclude FDA label" />
| routes_of_administration = [[口服給藥]]、[[靜脈注射]] (IV)、[[肌肉注射]] (IM)及[[皮下注射]] (SC)
| legal_EU = Rx-only
| legal_EU_comment = <ref>{{cite web | website=European Medicines Agency | title=Baraclude EPAR | date=2006-06-26 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/baraclude | access-date=2024-07-05 | archive-date=2024-03-06 | archive-url=https://web.archive.org/web/20240306150057/https://www.ema.europa.eu/en/medicines/human/EPAR/baraclude | url-status=live }}</ref>
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = Rx-only


<!-- Pharmacokinetic data -->
<!-- Pharmacokinetic data -->
| bioavailability = n/a (≥70)<ref name="Baraclude FDA label"/>
| bioavailability = 88%<ref name="DrugBank" />
| protein_bound = ~24–29% (其中5%至10%與{{le|人類血清白蛋白|Human serum albumin}}結合)<ref name="VolppHolzgrabe2019">{{cite journal | vauthors = Volpp M, Holzgrabe U | title = Determination of plasma protein binding for sympathomimetic drugs by means of ultrafiltration | journal = Eur J Pharm Sci | volume = 127 | issue = | pages = 175–184 | date = January 2019 | pmid = 30391401 | doi = 10.1016/j.ejps.2018.10.027 | url = }}</ref><ref name="Schmidt2023">{{cite thesis | vauthors = Schmidt S | title=Lang-etablierte Arzneistoffe genauer unter die Lupe genommen: Enantioselektive Proteinbindung und Stabilitätsstudien | trans-title = A closer look at long-established drugs: enantioselective protein binding and stability studies | language = de | publisher= Universität Würzburg | date=2023 | doi=10.25972/opus-34594 | page=}}</ref><ref name="GadAzabKhattab2021">{{cite journal | vauthors = Gad MZ, Azab SS, Khattab AR, Farag MA | title = Over a century since ephedrine discovery: an updated revisit to its pharmacological aspects, functionality and toxicity in comparison to its herbal extracts | journal = Food Funct | volume = 12 | issue = 20 | pages = 9563–9582 | date = October 2021 | pmid = 34533553 | doi = 10.1039/d1fo02093e | url = }}</ref>
| protein_bound = 13% ''([[in vitro]])''
| metabolism = 大部分未被代謝<ref name="DrugBank" /><ref name="ChuaBenrimojTriggs1989" />
| metabolism = 可忽略不計
| metabolites = • [[苯丙醇胺]]<ref name="DrugBank" /><ref name="ChuaBenrimojTriggs1989">{{cite journal | vauthors = Chua SS, Benrimoj SI, Triggs EJ | title = Pharmacokinetics of non-prescription sympathomimetic agents | journal = Biopharm Drug Dispos | volume = 10 | issue = 1 | pages = 1–14 | date = 1989 | pmid = 2647163 | doi = 10.1002/bdd.2510100102 | url = }}</ref>
| metabolites =
| onset = IV (幾秒內), IM (10-20分鐘), 口服 (15-60分鐘)<ref name="AHFS2016" />
| onset =
| elimination_half-life = 6{{nbsp}}hours<ref name="DrugBank">{{cite web | title=Ephedrine: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=2016-04-29 | url=https://go.drugbank.com/drugs/DB01364 | access-date=2024-07-14}}</ref>
| elimination_half-life = 128–149小時
| duration_of_action =
| duration_of_action = IV/IM (60分鐘), 口服 (2-4小時)
| excretion = [[腎]]臟（62–73%）
| excretion = 主要經[[尿]]液 (有60%為原形)<ref name="DrugBank" />


<!-- Identifiers -->
<!-- Identifiers -->
| index2_label = as sulfate
| CAS_number_Ref = {{cascite|changed|CAS}}
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 142217-69-4
| CAS_number = 299-42-3
| CAS_supplemental =
| CAS_number2_Ref = {{cascite|correct|CAS}}
| PubChem = 135398508
| CAS_number2 = 134-72-5
| IUPHAR_ligand =
| CAS_supplemental = <br />[https://commonchemistry.cas.org/detail?cas_rn=50-98-6 50-98-6] ([[hydrochloride]])
| PubChem = 9294
| IUPHAR_ligand = 556
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00442
| DrugBank = DB01364
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 135679
| ChemSpiderID = 8935
| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
| UNII_Ref = {{fdacite|changed|FDA}}
| ChemSpiderID2 = 4514262
| UNII = NNU2O4609D
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = GN83C131XS
| UNII2 = U6X61U5ZEG
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04008
| KEGG = D00124
| KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = D04018
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 473990
| ChEBI = 15407
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 713
| ChEMBL = 211456
| ChEMBL2_Ref = {{ebicite|correct|EBI}}
| NIAID_ChemDB =
| PDB_ligand =
| ChEMBL2 = 1523964
| synonyms = (−)-Ephedrine; (1''R'',2''S'')-Ephedrine; (1''R'',2''S'')-β-Hydroxy-''N''-methylamphetamine; (1''R'',2''S'')-β-Hydroxy-''N''-methyl-α-methyl-β-phenethylamine
| synonyms = ETV, BMS-200475-01


<!-- Chemical and physical data -->
<!-- Chemical data -->
| IUPAC_name = 2-Amino-9-[(1''S'',3''R'',4''S'')-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1''H''-purin-6-one
| IUPAC_name = (1''R'',2''S'')-2-(methylamino)-1-phenylpropan-1-ol
| C=12 | H=15 | N=5 | O=3
| C=10 | H=15 | N=1 | O=1
| SMILES = C=C1C(CC(C1CO)O)N2C=NC3=C2N=C(NC3=O)N
| SMILES = C[C@@H]([C@@H](C1=CC=CC=C1)O)NC
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20)/t6-,7-,8-/m0/s1
| StdInChI = 1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_comment =
| StdInChIKey = KWGRBVOPPLSCSI-WPRPVWTQSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = QDGZDCVAUDNJFG-FXQIFTODSA-N
| density =
| density_notes =
| melting_point = 220
| melting_high =
| melting_notes = 該值適用於恩替卡韋水合物，且為最小值<ref>{{cite encyclopedia |encyclopedia=The Merck Index |edition=14th |year=2006 |page=613 |isbn=978-0-911910-00-1 |title=The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals | vauthors = O'Neil MJ }}</ref>
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}}
}}


'''麻黃鹼'''（{{lang-en|ephedrine }}是一種[[中樞神經系統]] (簡稱CNS) [[興奮劑]]，常用於預防[[麻醉]]期間的[[低血壓]]。<ref name=AHFS2016>{{cite web|title=Ephedrine|url=https://www.drugs.com/monograph/ephedrine.html|publisher=The American Society of Health-System Pharmacists|access-date= 2017-09-08 |url-status=live|archive-url=https://web.archive.org/web/20170909053108/https://www.drugs.com/monograph/ephedrine.html|archive-date=2017-09-09}}</ref> 它也被用於治療[[氣喘]]、[[發作性嗜睡病]]和[[肥胖症]]，但均非首選藥物。<ref name=AHFS2016/>它在治療[[鼻塞]]的益處尚不清楚。給藥方式有[[口服給藥|口服]]、[[肌肉注射]]、[[靜脈注射]]或[[皮下注射]]。<ref name=AHFS2016/>靜脈注射後發生效用最快，肌肉注射將需20分鐘，口服則需要1小時才能發揮作用。<ref name=AHFS2016/>注射給藥時，其效力持續時間約為一小時，而口服時，其效力持續時間可達四小時。<ref name=AHFS2016/>
'''恩替卡韋'''（{{lang-en|entecavir}}）以商品名稱Baraluc（博路定）於市面上銷售，是一種[[抗病毒藥物]]，用於治療[[B型肝炎病毒]][[感染]]。<ref name=AHFS2016/>對於同時患有[[愛滋病]]和[[B型肝炎]]的患者，也應同時施用[[抗反轉錄病毒藥]]進行治療。<ref name=AHFS2016/>恩替卡韋以[[片劑]]或溶液形式，經[[口服給藥|口服]]方式給藥。<ref name=AHFS2016/>


使用後常見的副作用有睡眠困難、[[焦慮]]、[[頭痛]]、[[幻覺]]、[[高血壓]]、[[心跳過速]]、食慾不振和[[尿瀦留]]。<ref name=AHFS2016/>嚴重的副作用有[[中風]]和[[心肌梗塞]]。<ref name=AHFS2016/>雖然個體於[[妊娠|懷孕]]期間使用可能對於胎兒安全，但在該群體中的研究很少。<ref>{{cite book| vauthors = Briggs GG, Freeman RK, Yaffe SJ |title=Drugs in pregnancy and lactation : a reference guide to fetal and neonatal risk|date=2011|publisher=Lippincott Williams & Wilkins|location=Philadelphia|isbn=9781608317080|page=495|edition=9th|url=https://books.google.com/books?id=OIgTE4aynrMC&pg=PA495|url-status=live|archive-url= https://web.archive.org/web/20170908191457/https://books.google.com/books?id=OIgTE4aynrMC&pg=PA495 |archive-date=2017-09-08}}</ref><ref name=PB2016>{{cite web|title=Ephedrine Pregnancy and Breastfeeding Warnings|url=https://www.drugs.com/pregnancy/ephedrine.html|access-date=2017-10-08|url-status=live|archive-url=https://web.archive.org/web/20170805145931/https://www.drugs.com/pregnancy/ephedrine.html|archive-date=2017-08-05}}</ref>不建議在[[母乳哺育]]期間使用以確保嬰兒安全。<ref name=PB2016/>麻黃鹼通過誘導正腎上腺素的釋放而起作用，因此間接激活α[[腎上腺素受體]]和β腎上腺素受體。{{le|取代安非他命|Substituted amphetamine}}從化學角度來看，麻黃鹼是一種{{le|取代安非他命|Substituted amphetamine}}，並且是 (1R,2S)-β-羥基-N-甲基安非他命的對映異構體。{{le|取代安非他命|Substituted amphetamine}}
使用後常見的副作用有[[頭痛]]、[[噁心]]、[[高血糖]]和腎功能降低。<ref name=AHFS2016/>嚴重的副作用有[[肝腫大]]、[[乳酸性酸中毒]]以及停藥後出現[[肝炎]]炎。<ref name=AHFS2016/>為前述可能發生的嚴重副作用，[[美國食品藥物管理局]]（FDA）要求於藥物標籤中加上[[黑框警告]]。<ref>FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 2023-10-22.</ref>雖然個體於[[妊娠|懷孕]]期間使用似乎不會對於胎兒造成任何危害，但此方面尚未有充分研究，仍須謹慎。<ref name="Drugs.com pregnancy" />恩替卡韋是[[逆轉錄酶抑制劑]] (NRTI) 藥物家族中的一種。<ref name=AHFS2016/><ref>{{cite book| vauthors = Shetty K, Wu GY |title=Chronic Viral Hepatitis: Diagnosis and Therapeutics|date=2009|publisher=Springer Science & Business Media|isbn=9781597455657|page=34|url=https://books.google.com/books?id=o67J8smzgHEC&pg=PA34|language=en}}</ref>它透過阻斷[[反轉錄酶]]來防止B型肝炎病毒繁殖而發揮作用。<ref name=AHFS2016/>


恩替卡韋於2005年獲准用作醫療用途。<ref name=AHFS2016>{{cite web|title=Entecavir|url=https://www.drugs.com/monograph/entecavir.html|publisher=The American Society of Health-System Pharmacists|access-date=28 November 2016|url-status=live|archive-url=https://web.archive.org/web/20161220224057/https://www.drugs.com/monograph/entecavir.html|archive-date=2016-12-20}}</ref>它已被納入[[世界衛生組織基本藥物標準清單]]之中。<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref>市面上已有其[[通用名藥物]]流通。
麻黃鹼於1885年首次被成功萃取，並於1926年進入商業用途。<ref>{{cite book | vauthors = Soni MG, Shelke K, Amin R, Talati | chapter = A Lessons from the Use of Ephedra Products as a Dietary Supplement | veditors = Bagchi D, Preuss HG |title=Obesity epidemiology, pathophysiology, and prevention|date=2013|publisher=CRC Press|location=Boca Raton, Florida|isbn=9781439854266|page=692|edition=2nd|chapter-url=https://books.google.com/books?id=6oHRBQAAQBAJ&pg=PA692|url-status=live|archive-url=https://web.archive.org/web/20170908191457/https://books.google.com/books?id=6oHRBQAAQBAJ&pg=PA692|archive-date=2017-09-08}}</ref><ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=541 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA541 }}</ref>它已被納入[[世界衛生組織基本藥物標準清單]]之中。<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref>市面上有其[[通用名藥物]]流通。<ref name=AHFS2016/>它通常是[[麻黃屬]]植物中常見的物質。美國法律不允許含有[[麻黃鹼]]的非處方膳食補充劑販售，<ref name="AHFS2016" />但用於[[中藥學]]的補充劑除外，用"má huáng（麻黃）"指出其中含有此種物質。<ref name=AHFS2016/><ref name="AbourashedEl-AlfyKhan2003">{{cite journal | vauthors = Abourashed EA, El-Alfy AT, Khan IA, Walker L | s2cid = 41083359 | title = Ephedra in perspective—a current review | journal = Phytotherapy Research | volume = 17 | issue = 7 | pages = 703–712 | date = August 2003 | pmid = 12916063 | doi = 10.1002/ptr.1337 }}</ref>


==醫療用途==
==醫療用途==
[[Image:EphedrineInBottles.jpg|thumb|right|硫酸鹽麻黃鹼（1932年）、麻黃鹼合成物（1932年）及Swan-Myers藥廠出品的66號麻黃鹼吸入劑（約1940年）。]]
恩替卡韋主要用於治療成人和兩歲及以上兒童，具有活躍病毒複製且肝功能異常之慢性B型肝炎患者。<ref name="Baraclude FDA label">{{cite web | title=Baraclude- entecavir tablet, film coated Baraclude- entecavir solution | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=046e61c9-9298-4b2e-b76e-b26b81fecd20 | access-date= 2021-01-24 | archive-date=2016-11-08 | archive-url=https://web.archive.org/web/20161108140245/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=046e61c9-9298-4b2e-b76e-b26b81fecd20 | url-status=live }}</ref>它也用於預防肝臟移植後發生的B型肝炎病毒的再感染，<ref>{{cite journal | vauthors = Fung J, Cheung C, Chan SC, Yuen MF, Chok KS, Sharr W, Dai WC, Chan AC, Cheung TT, Tsang S, Lam B, Lai CL, Lo CM | title = Entecavir monotherapy is effective in suppressing hepatitis B virus after liver transplantation | journal = Gastroenterology | volume = 141 | issue = 4 | pages = 1212–1219 | date = October 2011 | pmid = 21762659 | doi = 10.1053/j.gastro.2011.06.083 | doi-access = free }}</ref>以及治療同時感染B型肝炎病毒的愛滋病患者。雖然恩替卡韋對愛滋病具有較弱的治療活性，但在無完全抑制性抗反轉錄病毒治療下，不建議單獨使用恩替卡韋於愛滋病/B型肝炎共感染患者。<ref>{{cite web|title=Guidelines for the use of antiretroviral agents in HIV-1-infected adults and adolescents|url=http://aidsinfo.nih.gov/contentfiles/lvguidelines/adultandadolescentgl.pdf|publisher=Panel on Antiretroviral Guidelines for Adults and Adolescents|access-date=2015-03-15|url-status=live|archive-url=https://web.archive.org/web/20161101202407/https://aidsinfo.nih.gov/contentfiles/lvguidelines/adultandadolescentgl.pdf|archive-date= 2016-11-01}}</ref>因為單獨使用恩替卡韋可能會選擇性地導致艾滋病病毒對[[拉米夫定]]和[[恩曲他濱]]（兩者皆為抗反轉錄藥物）產生抗藥性。<ref>{{cite journal | vauthors = McMahon MA, Jilek BL, Brennan TP, Shen L, Zhou Y, Wind-Rotolo M, Xing S, Bhat S, Hale B, Hegarty R, Chong CR, Liu JO, Siliciano RF, Thio CL | title = The HBV drug entecavir - effects on HIV-1 replication and resistance | journal = The New England Journal of Medicine | volume = 356 | issue = 25 | pages = 2614–2621 | date = June 2007 | pmid = 17582071 | pmc = 3069686 | doi = 10.1056/NEJMoa067710 }}</ref>


麻黃鹼是一種非[[兒茶酚胺]][[擬交感神經藥]]，其心血管作用與[[腎上腺素]]相似：可升高血壓、心跳和心肌收縮力。麻黃鹼與[[偽麻黃鹼]]一樣，是一種[[支氣管擴張藥]]，但偽麻黃鹼的作用要小很多。<ref name=Butterworth2022>{{cite book | vauthors = Butterworth IV JF, Mackey DC, Wasnick JD | chapter = Chapter 14. Adrenergic Agonists & Antagonists. | title = Morgan & Mikhail's Clinical Anesthesiology | edition = 7th | date = 2022 | publisher = McGraw-Hill Education | chapter-url = https://accessanesthesiology.mhmedical.com/content.aspx?bookid=3194&sectionid=266518784 | isbn = 978-1-260-47379-7 }}</ref><ref name='drew'>{{cite journal | vauthors = Drew CD, Knight GT, Hughes DT, Bush M | title = Comparison of the effects of D-(-)-ephedrine and L-(+)-pseudoephedrine on the cardiovascular and respiratory systems in man | journal = British Journal of Clinical Pharmacology | volume = 6 | issue = 3 | pages = 221–5 | date = September 1978 | pmid = 687500 | pmc = 1429447 | doi = 10.1111/j.1365-2125.1978.tb04588.x }}</ref>
恩替卡韋的療效已經多項隨機、雙盲、多中心試驗的研究中證實。口服形式的恩替卡韋是有效且使用者耐受性良好的藥物。<ref name="enteca">{{cite journal | vauthors = Scott LJ, Keating GM | title = Entecavir: a review of its use in chronic hepatitis B | journal = Drugs | volume = 69 | issue = 8 | pages = 1003–1033 | date = May 2009 | pmid = 19496629 | doi = 10.2165/00003495-200969080-00005 | s2cid = 115493805 | url = http://adisonline.com/drugs/abstract/2009/69080/Entecavir__A_Review_of_its_Use_in_Chronic.5.aspx | url-status = dead | access-date = 2010-03-29 | archive-url = https://web.archive.org/web/20111008153846/http://adisonline.com/drugs/abstract/2009/69080/Entecavir__A_Review_of_its_Use_in_Chronic.5.aspx | archive-date = 2011-10-08 }}</ref>


麻黃鹼可以減少[[暈動病]]，但它主要用於減少其他用於暈動病的藥物的鎮靜作用。<ref>{{cite book | vauthors = Buckey Jr JC |title=Space Physiology |date=2006 |publisher=Oxford University Press |isbn= 978-0-1997-4790-0 |page=201 |url= https://books.google.com/books?id=Jn_i6KbutXYC&pg=PA201 }}</ref><ref>{{cite book | vauthors = Sanford CA, Jong EC |title=The Travel and Tropical Medicine Manual E-Book |date=2008 |publisher=Elsevier Health Sciences |isbn=978-1437710694 |page=139 |url= https://books.google.com/books?id=gAz-_hBG90sC&pg=PA139 }}</ref>
===懷孕時期與母乳哺育時期使用===

目前尚無對此充分且良好對照研究，相關個體在使用時應謹慎。<ref name="Drugs.com pregnancy" />
麻黃鹼也被發現對幼兒期{{le|先天性肌無力症候群|Congenital myasthenic syndrome}}具有快速且持久的反應性，甚至對具有新型{{le|COLQ基因|COLQ}}突變的成年人（會導致[[重症肌無力]]）也具有快速且持久的反應性。<ref>{{Cite journal| vauthors = Higashida K, Yamada M, Shimohata T |date=2021-04-13|title=Quick and long-lasting responsiveness by ephedrine in an adult woman with congenital myasthenic syndrome associated with a novel COLQ mutation. (2928) |url= https://n.neurology.org/content/96/15_Supplement/2928 |journal=Neurology|volume=96|issue=15 Supplement|doi=10.1212/WNL.96.15_supplement.2928 |s2cid=266124150 |issn=0028-3878}}</ref>

經由靜脈快速推注給藥後，重新給藥時通常需要增加劑量以抵消[[急速耐藥性]]的發生，這是由於持續刺激導致個體兒茶酚胺耗竭所致，而產生藥物耐受性。<ref name=Butterworth2022/>

===減肥===
麻黃鹼因尤其可降低體脂肪，可達到短期適度減肥的目的，<ref>{{cite journal | vauthors = Shekelle PG, Hardy ML, Morton SC, Maglione M, Mojica WA, Suttorp MJ, Rhodes SL, Jungvig L, Gagné J | display-authors = 6 | title = Efficacy and safety of ephedra and ephedrine for weight loss and athletic performance: a meta-analysis | journal = JAMA | volume = 289 | issue = 12 | pages = 1537–45 | date = March 2003 | pmid = 12672771 | doi = 10.1001/jama.289.12.1470 }}</ref>但此藥物的長期影響尚不清楚。<ref>{{cite journal | vauthors = Dwyer JT, Allison DB, Coates PM | title = Dietary supplements in weight reduction | journal = Journal of the American Dietetic Association | volume = 105 | issue = 5 Suppl 1 | pages = S80-6 | date = May 2005 | pmid = 15867902 | doi = 10.1016/j.jada.2005.02.028 | url = https://zenodo.org/record/1259087 }}</ref>在{{le|小鼠|mouse}}身上的實驗，已知麻黃鹼會刺激[[棕色脂肪組織]]中的[[產熱]]作用，但由於成年人只有少量棕色脂肪，因此推測產熱主要發生在[[骨骼肌]]中。麻黃鹼可降低胃排空的速度。[[咖啡因]]和[[茶鹼]]等[[黃嘌呤]]與麻黃鹼在減肥方面具協同作用，而導致商家創建及行銷三者複合的產品。<ref name="BrayBouchard2004">{{cite book | vauthors = Bray GA, Bouchard C |title=Handbook of obesity |url= https://books.google.com/books?id=YVQPOfKYJhUC&pg=PA494 |year=2004 |publisher= CRC Press |isbn=978-0-8247-4773-2 |pages=494–496 |url-status=live |archive-url= https://web.archive.org/web/20140626190101/http://books.google.com/books?id=YVQPOfKYJhUC&pg=PA494 |archive-date= 2014-06-26}}</ref>其中一種被稱為{{le|ECA stack|ECA stack}}，含有麻黃鹼、咖啡因和[[阿斯匹靈]]，是參與[[健美]]比賽者在賽前減少體內脂肪常用的補充劑。 <ref>{{cite journal | vauthors = Magkos F, Kavouras SA | title = Caffeine and ephedrine: physiological, metabolic and performance-enhancing effects | journal = Sports Medicine | volume = 34 | issue = 13 | pages = 871–89 | year = 2004 | pmid = 15487903 | doi = 10.2165/00007256-200434130-00002 | s2cid = 1966020 }}</ref>於2021年所作的一項[[系統性回顧]]發現個體使用麻黃鹼可比使用[[安慰劑]]者減輕2公斤的體重（4.4磅），提高[[心率]]，降低[[低密度脂蛋白]]水平，提高[[高密度脂蛋白]]水平，但[[血壓]]方面無統計學上的顯著差異。<ref>{{cite journal | vauthors = Yoo HJ, Yoon HY, Yee J, Gwak HS | title = Effects of Ephedrine-Containing Products on Weight Loss and Lipid Profiles: A Systematic Review and Meta-Analysis of Randomized Controlled Trials | journal = Pharmaceuticals | volume = 14 | issue = 11 | pages = 1198 | date = November 2021 | pmid = 34832979 | pmc = 8618781 | doi = 10.3390/ph14111198 | doi-access = free }}</ref>

===市售配方===
麻黃鹼在美國是以靜脈注射液形式的處方藥銷售，品牌名稱有Akovaz、Corphedra、Emerphed和 Rezipres以及通用名藥物。<ref name="Drugs@FDA">{{cite web | title=Drugs@FDA: FDA-Approved Drugs | publisher = Food and Drug Administration | website=accessdata.fda.gov | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm | access-date=2024-07-14}}</ref><ref name="DailyMed">{{cite web | title=Search Results for ephedrine | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/search.cfm?query=ephedrine&searchdb=all&labeltype=all&sortby=rel&audience=professional&page=1&pagesize=200 | access-date=2024-07-14}}</ref>也有非處方藥以12.5和 25毫克口服片劑形式，用作支氣管擴張劑和用作{{le|舒緩鼻塞藥|decongestant}}的0.5%濃度{{le|鼻噴劑|nasal spray}}。<ref name="DailyMed" />麻黃鹼也可與[[癒創甘油醚]]組成複方的口服片劑和藥水。<ref name="DailyMed" />麻黃鹼在藥品中通常以鹽酸鹽或硫酸鹽的形式存在，以增加其穩定性和溶解度。<ref name="Drugs@FDA" /><ref name="DailyMed" />

==禁忌症==
麻黃鹼不可與某些[[抗憂鬱劑]]（即[[去甲腎上腺素-多巴胺再吸收抑制劑]]（NDRI））一起使用，因為這會增加因血清[[正腎上腺素]]（又稱去甲腎上腺素）水平過高而可能導致一系列併發症。

[[安非他酮]]是一種抗憂鬱藥，具有與麻黃鹼相似的[[苯丙胺]]樣結構，是一種NDRI。其作用更類似[[苯丙胺|安非他命]]，而非[[氟西汀]]，因為它的主要治療作用涉及正腎上腺素，在較小程度上涉及[[多巴胺]]，但它也會從突觸前裂釋放一些血清素。它不應與麻黃鹼一起使用，因為可能會增加副作用的可能性。

麻黃鹼應謹慎用於以下患者：<ref name =Mayne>Mayne Pharma. Ephedrine sulfate injection DBL (Approved Product Information). Melbourne: Mayne Pharma; 2004</ref>
*水分補充不足者
*腎上腺功能障礙者
*[[缺氧]]者
*[[高碳酸血症]]者
*[[酸中毒]]者
*高血壓患者
*[[甲狀腺機能亢進]]者
*[[良性前列腺增生症|攝護腺肥大症]]者
*[[糖尿病]]患者
*[[心血管疾病]]患者
*孕婦於分娩期間，血壓超過130/80毫米汞柱時
*進行母乳哺育的女性
個體於懷孕期間使用麻黃鹼可能對胎兒造成潛在風險，因此一般不建議使用。 只有在病情嚴重，且其他藥物無法作用的情況下，才可能在醫師的評估下謹慎進行。<ref name =Mayne />


==副作用==
==副作用==
麻黃鹼是一種有潛在危險性的天然化合物，截至2004年，[[美國食品藥物管理局]]（FDA）已收到超過18,000份有關使用後出現不良反應的報告。<ref name="Palamar2011" />
大多數使用恩替卡韋的個體幾乎沒副作用發生。<ref>{{cite web|url=https://www.drugs.com/cdi/entecavir.html|title=Entecavir: Indications, Side Effects, Warnings - Drugs.com|website=www.drugs.com|access-date=2016-11-10|url-status=live|archive-url=https://web.archive.org/web/20161107161241/https://www.drugs.com/cdi/entecavir.html|archive-date=2016-11-07}}</ref>如果有的話，最常見的是頭痛、疲勞、[[頭暈]]和噁心。<ref name="Baraclude FDA label"/>較不常見的副作用有[[失眠]]和消化道症狀，如胃酸過多、[[腹瀉]]和[[嘔吐]]。<ref>{{cite web|url=https://www.drugs.com/sfx/entecavir-side-effects.html|title=Entecavir Side Effects in Detail - Drugs.com|website=www.drugs.com|access-date=2016-11-10|url-status=live|archive-url=https://web.archive.org/web/20161110172702/https://www.drugs.com/sfx/entecavir-side-effects.html|archive-date=2016-11-10}}</ref>

全身給藥（例如注射或口服方式）的[[藥物不良反應]]（ADR）較局部給藥（如鼻腔噴藥）更為常見。與麻黃鹼治療相關的不良反應包含有：<ref name=JFC>Joint Formulary Committee. [[British National Formulary]], 47th edition. London: British Medical Association and Royal Pharmaceutical Society of Great Britain; 2004. {{ISBN|0-85369-587-3}}</ref>
*心血管：心條過速、[[心律不整]]、[[心絞痛]]、高血壓引起的[[血管收縮]]
*[[皮膚病學|皮膚]]：潮紅、出汗、[[痤瘡]]
*[[消化道]]：噁心
*[[泌尿生殖系統]]：由於腎動脈血管收縮而導致排尿減少，排尿困難並不罕見，因為麻黃鹼等{{le|α-腎上腺素受體激動劑|Alpha-adrenergic agonist}}會收縮[[尿道括約肌]]，此作用類似於[[交感神經]]系統活化時對泌尿系統的影響。
*[[神經系統]]：煩躁、{{le|精神錯亂|Confusion}}、失眠、輕度[[欣快感]]、躁狂/幻覺（罕見，除先前存在精神疾病外）、[[妄想]]、{{le|蟻走感|formication}}（可能有，但缺乏書面證據）[[偏執狂]]、[[敵意]]、[[恐慌]]、{{le|激動|agitation}}
*[[呼吸系統]]：[[呼吸困難]]、肺水腫
*其他：頭暈、頭痛、震顫、[[高血糖]]反應、口乾

==過量==
使用過量的麻黃鹼會引起血壓快速上升。個體發生使用過量的情況時，須時時檢測血壓，必要時可注射型降血壓藥處理，如果有呼吸急促或出現[[發紺]]，須確保患者氣道暢通並提供[[機械換氣]]。<ref>{{cite web| url =https://www.ncbi.nlm.nih.gov/books/NBK547661/|title =Ephedrine | publisher =StatPearls [Internet]|author=Alec K. Statler; Christopher V. Maani; Arpan Kohli. | date = | accessdate = 2024-09-02 }}</ref>

==藥物交互作用==
麻黃鹼與[[單胺氧化酶抑制劑]]（MAOIs）如{{le|苯乙肼|Phenelzine}}和[[反苯環丙胺]]一起使用可能會導致{{le|高血壓危機|Hypertension crisis}}。<ref>{{cite journal |last1=Edinoff |first1=Amber N. |last2= Swinford |first2=Connor R. |date=2022-011-03 |title= Clinically Relevant Drug Interactions with Monoamine Oxidase Inhibitors
|url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9680847/ |journalHealth Psychology Research |volume=10 |issue= 4|pages=39576 |doi=10.52965/001c.39576 |access-date=2024-09-02}}</ref>

==藥理學==
===藥效學===
麻黃鹼是一種[[擬交感神經藥]]，作用於部分交感神經系統 (SNS)。其主要作用機制依賴於其間接刺激腎上腺素受體系統，通過增加正腎上腺素在突觸後α和β受體上的活性。<ref name=merck>{{cite web | url = http://www.merckmanuals.com/professional/lexicomp/ephedrine.html | date = January 2010 | work = Merck Manuals | title = EPHEDrine | archive-url = https://web.archive.org/web/20110324031411/http://www.merckmanuals.com/professional/lexicomp/ephedrine.html | archive-date = 2011-03-24 }}</ref>與α受體直接相互作用的可能性不大，但仍有爭議。<ref name="Docherty2008" /><ref name='drew'/><ref name="Ma_2007">{{cite journal | vauthors = Ma G, Bavadekar SA, Davis YM, Lalchandani SG, Nagmani R, Schaneberg BT, Khan IA, Feller DR | display-authors = 6 | title = Pharmacological effects of ephedrine alkaloids on human alpha(1)- and alpha(2)-adrenergic receptor subtypes | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 322 | issue = 1 | pages = 214–221 | date = July 2007 | pmid = 17405867 | doi = 10.1124/jpet.107.120709 | s2cid = 86429875 }}</ref><ref name="pmid14570629">{{cite journal | vauthors = Kobayashi S, Endou M, Sakuraya F, Matsuda N, Zhang XH, Azuma M, Echigo N, Kemmotsu O, Hattori Y, Gando S | display-authors = 6 | title = The sympathomimetic actions of l-ephedrine and d-pseudoephedrine: direct receptor activation or norepinephrine release? | journal = Anesthesia and Analgesia | volume = 97 | issue = 5 | pages = 1239–1245 | date = November 2003 | pmid = 14570629 | doi = 10.1213/01.ANE.0000092917.96558.3C | doi-access = free }}</ref>左旋麻黃鹼，特別是其立體異構體[[去甲偽麻黃鹼]]（也存在於麻黃鹼中）具有間接擬交感神經作用，並且由於其能夠穿過[[血腦屏障]]，因此它是一種類似於安非他命的中樞神經系統興奮劑，但不太明顯，因為它在大腦中釋放正腎上腺素和多巴胺，與安非他命的釋放位置不同。<ref>{{cite journal | vauthors = Munhall AC, Johnson SW | title = Dopamine-mediated actions of ephedrine in the rat substantia nigra | journal = Brain Research | volume = 1069 | issue = 1 | pages = 96–103 | date = January 2006 | pmid = 16386715 | doi = 10.1016/j.brainres.2005.11.044 | s2cid = 40626692 }}</ref>

===藥物動力學===
====吸收====
麻黃鹼的口服劑[[生物利用度]]為88%。口服後15至60分鐘開始作用，肌肉注射後10至20分鐘開始作用，靜脈輸注後則在數秒內開始作用。<ref name="AHFS2016" />

====分佈====
此藥物的[[血漿蛋白結合]]率約為24%至29%，其中5%至10%與{{le|人類血清白蛋白|Human serum albumin}}結合。<ref name="VolppHolzgrabe2019">{{cite journal | vauthors = Volpp M, Holzgrabe U | title = Determination of plasma protein binding for sympathomimetic drugs by means of ultrafiltration | journal = Eur J Pharm Sci | volume = 127 | issue = | pages = 175–184 | date = January 2019 | pmid = 30391401 | doi = 10.1016/j.ejps.2018.10.027 | url = }}</ref><ref name="Schmidt2023">{{cite thesis | vauthors = Schmidt S | title=Lang-etablierte Arzneistoffe genauer unter die Lupe genommen: Enantioselektive Proteinbindung und Stabilitätsstudien | trans-title = A closer look at long-established drugs: enantioselective protein binding and stability studies | language = de | publisher= Universität Würzburg | date=2023 | doi=10.25972/opus-34594 | page=}}</ref><ref name="GadAzabKhattab2021">{{cite journal | vauthors = Gad MZ, Azab SS, Khattab AR, Farag MA | title = Over a century since ephedrine discovery: an updated revisit to its pharmacological aspects, functionality and toxicity in comparison to its herbal extracts | journal = Food Funct | volume = 12 | issue = 20 | pages = 9563–9582 | date = October 2021 | pmid = 34533553 | doi = 10.1039/d1fo02093e | url = }}</ref>

====代謝====
大部分麻黃鹼不會被代謝。正腎上腺素（[[苯丙醇胺]]）是麻黃鹼經由N-去甲基化形成的活性代謝物。<ref name="DrugBank" /><ref name="ChuaBenrimojTriggs1989">{{cite journal | vauthors = Chua SS, Benrimoj SI, Triggs EJ | title = Pharmacokinetics of non-prescription sympathomimetic agents | journal = Biopharm Drug Dispos | volume = 10 | issue = 1 | pages = 1–14 | date = 1989 | pmid = 2647163 | doi = 10.1002/bdd.2510100102 | url = }}</ref>口服劑的麻黃鹼中約8%至20%去甲基化為正腎上腺素，約4%至13%[[氧化還原反應|氧化]][[去胺作用|脫氨]]為[[苯甲酸]]，一小部分轉化為1,2-二羥基-1-苯基丙烷。<ref name="ChuaBenrimojTriggs1989" />

====消除====
麻黃鹼主要經由[[尿]]液排出體外，其中60%（範圍 53-79%）以原形排出。<ref name="ChuaBenrimojTriggs1989" />

麻黃鹼的[[生物半衰期]]為6小時。<ref name="DrugBank" />口服作用時間為2至4小時，靜脈或肌肉注射作用持續時間為60分鐘。

==化學==
麻黃鹼是一種擬交感神經藥和取代安非他命。它的分子結構與[[苯丙醇胺]]、[[甲基苯丙胺|甲基安非他命]]和腎上腺素相似。從化學角度來看，它是一種具有[[苯乙胺]]骨架的[[生物鹼]]，存在於麻黃屬的各種植物中。它主要透過增加腎上腺素受體上正腎上腺素的活性來發揮作用。[28][33]此藥物通常以鹽酸鹽或硫酸鹽的形式銷售。

鹽酸鹽麻黃鹼的熔點為187−188°C。<ref name="ChuaBenrimojTriggs1989" />
[[File:Ephedrine and pseudoephedrine isomers.svg|thumb|400px|麻黃鹼的四種立體異構體。]]

===體液檢測===
麻黃鹼可在人體血液、血漿或尿液中進行定量檢測，以監測運動員可能的濫用，確認中毒診斷或協助法醫進行死因調查。許多針對安非他命的商業[[免疫分析]]篩檢與麻黃鹼明顯發生交叉反應，但利用[[層析|色層分析法]]可輕鬆將麻黃鹼和其他苯乙胺衍生物區分。服用該藥物患者的血液或血漿麻黃鹼濃度通常在20-200維克/升（μg/L）的範圍，濫用者或中毒患者的在300-3,000維克/升的範圍，在急性致命過量用藥情況下的在3-20毫克/升的範圍。目前[[世界反運動禁藥機構]](WADA) 對運動員尿液中麻黃鹼設定的底線標準為10維克/升。<ref>{{cite web |url= http://list.wada-ama.org/list/s6-stimulants |title=S6. Stimulants &#124; List of Prohibited Substances and Methods |access-date= 2015-10-19 |url-status=dead |archive-url= https://web.archive.org/web/20151023042222/http://list.wada-ama.org/list/s6-stimulants/ |archive-date=2015-10-23 }}</ref><ref>{{cite journal | vauthors = Schier JG, Traub SJ, Hoffman RS, Nelson LS | title = Ephedrine-induced cardiac ischemia: exposure confirmed with a serum level | journal = Journal of Toxicology. Clinical Toxicology | volume = 41 | issue = 6 | pages = 849–53 | year = 2003 | pmid = 14677795 | doi = 10.1081/clt-120025350 | s2cid = 23359388 }}</ref><ref>WADA. ''The World Anti-Doping Code'', World Anti-Doping Agency, Montreal, Canada, 2010. [http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/WADA_Prohibited_List_2010_EN.pdf url] {{webarchive|url=https://web.archive.org/web/20130911050811/http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/WADA_Prohibited_List_2010_EN.pdf |date=2013-09-11 }}</ref><ref>{{cite book | vauthors = Baselt R | title = Disposition of Toxic Drugs and Chemicals in Man | edition = 8th | publisher = Biomedical Publications | location = Foster City, CA | date = 2008 | pages = 542–544 }}</ref>

==歷史==
===亞洲===
[[中醫學]]將天然形式的麻黃鹼稱為“麻黃（máhuáng）”，自[[漢朝]]（公元前206年至公元220年）起就被作為一種平緩氣喘劑和興奮劑來使用。<ref name="principles">{{cite book| vauthors = Levy WO, Kalidas K | veditors = Miller NS |title=Principles of Addictions and the Law: Applications in Forensic, Mental Health, and Medical Practice|date=26 February 2010|publisher=Academic Press|isbn=978-0-12-496736-6|pages=307–308}}</ref>傳統中醫在過去幾個世紀均將麻黃用來治療氣喘和支氣管炎。<ref name=Ford>{{cite book | veditors = Ford MD, Delaney KA, Ling LJ, Erickson T | title = Clinical Toxicology | location = Philadelphia | publisher = WB Saunders | date = 2001 | isbn = 0-7216-5485-1}}</ref>

[[日本]][[有機化學]]家{{le|永井長吉|Nagai Nagayoshi}}於1885年根據其對日本和[[中國]]傳統草藥的研究，首先以化學合成方式造出麻黃鹼。
中國以工業化方式生產麻黃鹼始於1920年代，由[[默克]]製藥以麻黃素的名義推廣和銷售這種藥物。 中國於1926年至1928年的兩年間向西方出口的麻黃素從4噸增加到216噸。<ref name="Dikotter">{{cite book | vauthors = Dikotter F, Laamann LP |title= Narcotic Culture: A History of Drugs in China |date=16 April 2004 |publisher=University of Chicago Press |isbn=978-0-226-14905-9 |page= 199 }}</ref>

===西醫===
麻黃鹼於1926年首次在美國被引入醫療用途。<ref name="Palamar2011">{{cite journal | vauthors = Palamar J | title = How ephedrine escaped regulation in the United States: a historical review of misuse and associated policy | journal = Health Policy | volume = 99 | issue = 1 | pages = 1–9 | date = January 2011 | pmid = 20685002 | doi = 10.1016/j.healthpol.2010.07.007 | url = }}</ref>

美國[[Vicks|Vicks]]製藥於1948年推出一款含有硫酸麻黃鹼作為活性成分的滴鼻劑上市（商品名Vatronol），可快速緩解鼻充血，此產品現已停止銷售。

==社會與文化==
===休閒用途===
[[Image:Ephedrine - 10 x 30mg.jpg|thumb|right|麻黃鹼片劑]]

麻黃鹼一種是苯乙胺，其化學結構與安非他命類似，是一種甲基安非他命類似物，具有甲基安非他命結構，且β位有羥基。由於麻黃鹼的結構與甲基安非他命相似，因此可透過化學還原除去麻黃鹼的羥基來製造甲基安非他命；使得麻黃鹼成為非法製造甲基安非他命備受追捧的前驅物。

將麻黃鹼還原為甲基安非他命的最流行方法與[[伯奇還原反應]]類似。第二種最受歡迎的方法是使用紅[[磷]]和[[碘]]與麻黃鹼反應。此外，麻黃鹼可透過簡單的氧化合成[[甲卡西酮]]（被《[[精神藥物公約]]》和[[受管制物質法案]]列為表一類受管制物質）。因此麻黃鹼被《[[聯合國禁止非法販運麻醉藥品和精神藥物公約]]》列為表一類[[前體藥物]]。

===運動和體能活動用途===
麻黃鹼經常被用作運動和體能活動中的[[表現增強物質]]。<ref name="Docherty2008">{{cite journal | vauthors = Docherty JR | title = Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA) | journal = Br J Pharmacol | volume = 154 | issue = 3 | pages = 606–622 | date = June 2008 | pmid = 18500382 | pmc = 2439527 | doi = 10.1038/bjp.2008.124 | url = }}</ref><ref name="Lieberman2001">{{cite journal | vauthors = Lieberman HR | title = The effects of ginseng, ephedrine, and caffeine on cognitive performance, mood and energy | journal = Nutr Rev | volume = 59 | issue = 4 | pages = 91–102 | date = April 2001 | pmid = 11368507 | doi = 10.1111/j.1753-4887.2001.tb06995.x | url = }}</ref><ref name="MagkosKayouras2004">{{cite journal | vauthors = Magkos F, Kavouras SA | title = Caffeine and ephedrine: physiological, metabolic and performance-enhancing effects | journal = Sports Med | volume = 34 | issue = 13 | pages = 871–889 | date = 2004 | pmid = 15487903 | doi = 10.2165/00007256-200434130-00002 | url = }}</ref><ref name="Graham2001">{{cite journal | vauthors = Graham TE | title = Caffeine, coffee and ephedrine: impact on exercise performance and metabolism | journal = Can J Appl Physiol | volume = 26 Suppl | issue = | pages = S103–S119 | date = 2001 | pmid = 11897887 | doi = | url = }}</ref>它可以提高心率、血壓和心肌收縮力，並作為一種興奮劑。<ref name="Docherty2008" />麻黃鹼通常與咖啡因一起用於增強體能表現。<ref name="MagkosKayouras2004" /><ref name="Graham2001" />

===其他用途===
在化學合成中，麻黃鹼被大量用於[[手性助劑]]的用途。<ref name=UN>[http://www.incb.org/pdf/e/list/red.pdf Microsoft Word – RedListE2007.doc<!-- Bot generated title -->] {{webarchive |url= https://web.archive.org/web/20080227224025/http://www.incb.org/pdf/e/list/red.pdf |date=February 27, 2008 }}</ref>
[[Image:EphedrineChiralAuxiliary.svg|600px|center|thumb|麻黃鹼作為手性助劑用途。]]

在合成[[沙奎那韋]]（一種[[抗反轉錄病毒藥物]]）的過程中，為分離出具有特定結構的半酸分子，科學家會將它與左旋麻黃鹼結合形成鹽。這個鹽的形成有助於將需要的半酸從其他物質中分離出來。

===法律地位===
====加拿大====
[[加拿大衛生部]]於2002年1月發佈自願召回令，將所有每劑含量超過8毫克的麻黃鹼產品、所有麻黃鹼與其他興奮劑（例如咖啡因）的組合以及所有用於減肥或健美適應症的麻黃鹼產品收回，理由是存在嚴重健康風險。<ref name="health-canada">{{cite web |url = http://www.hc-sc.gc.ca/ahc-asc/media/advisories-avis/2002/2002_01_e.html |title= Health Canada requests recall of certain products containing Ephedra/ephedrine |publisher=[[Health Canada]] |date= January 9, 2002 |access-date= July 7, 2009 |archive-url= https://web.archive.org/web/20070206073244/http://www.hc-sc.gc.ca/ahc-asc/media/advisories-avis/2002/2002_01_e.html |archive-date= February 6, 2007}}</ref> Ephedrine is still sold as an oral nasal decongestant<ref name= "LaccourreyeWerner2015">{{cite journal | vauthors = Laccourreye O, Werner A, Giroud JP, Couloigner V, Bonfils P, Bondon-Guitton E | title = Benefits, limits and danger of ephedrine and pseudoephedrine as nasal decongestants | journal = European Annals of Otorhinolaryngology, Head and Neck Diseases | volume = 132 | issue = 1 | pages = 31–4 | date = February 2015 | pmid = 25532441 | doi = 10.1016/j.anorl.2014.11.001 | doi-access = free }}</ref>麻黃鹼仍以口服舒緩鼻塞藥，以8毫克片劑的形式作為天然保健品出售，每包的麻黃鹼含量限量為0.4克（400毫克），這是加拿大《管制藥物和物質法》規定的成分上限，麻黃鹼被認為是A類前驅藥物。<ref>{{Cite web|author=Legislative Services Branch|date=2021-03-18|title=Consolidated federal laws of canada, Controlled Drugs and Substances Act|url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/page-18.html|access-date=2021-07-30|website=laws-lois.justice.gc.ca|archive-date=2021-07-30|archive-url=https://web.archive.org/web/20210730190944/https://laws-lois.justice.gc.ca/eng/acts/c-38.8/page-18.html|url-status=dead}}</ref>

====美國====
FDA於1997年提出一項關於麻黃（可萃取麻黃鹼的草藥）的法規，將麻黃劑量限制為8毫克（活性麻黃鹼），每天用量不超過24毫克。<ref>[https://web.archive.org/web/20080102053737/http://www.cfsan.fda.gov/~lrd/fr97064a.html Federal Register: June 4, 1997 (Volume 62, Number 107): Dietary Supplements Containing Ephedrine Alkaloids; Proposed Rule]</ref>該擬議規則於2000年被撤回，部分原因是"該機構所提出的特定膳食成分含量和產品使用期限的依據，受到廣泛質疑。”<ref>[https://web.archive.org/web/20080126192127/http://www.cfsan.fda.gov/~lrd/fr00043a.html Federal Register: April 3, 2000 (Volume 65, Number 64): Dietary Supplements Containing Ephedrine Alkaloids; Withdrawal in Part]</ref>FDA於2004年對非哮喘、感冒、過敏、其他疾病或傳統亞洲使用的麻黃鹼生物鹼發佈禁令。<ref>[https://web.archive.org/web/20070929121300/http://www.cfsan.fda.gov/~lrd/fr040211.html Federal Register: February 11, 2004 (Volume 69, Number 28): Final Rule Declaring Dietary Supplements Containing Ephedrine Alkaloids Adulterated Because They Present an Unreasonable Risk; Final Rule]</ref>[[美國猶他聯邦地區法院]]於2005年4月14日裁定FDA沒適當的證據表明低劑量麻黃鹼生物鹼實際上是不安全的，<ref>{{cite web |url= http://www.ephedrinehydrochloride.com/204cv409-28.pdf |title=Nutraceutical Corporation; Solaray, Inc., Plaintiffs-appellees, v. Andrew Von Eschenbach, Acting Commissioner, U.S. Food and Drug Administration; United States Food and Drug Administration; Michael O. Leavitt, Secretary of the Department of Health and Human Services; Department of Health and Human Services; United States of America | quote = Defendants-appellants, 459 F.3d 1033 (10th Cir. 2006) |access-date= 2010-07-01 |url-status=dead |archive-url= https://web.archive.org/web/20110710194438/http://www.ephedrinehydrochloride.com/204cv409-28.pdf |archive-date= 2011-07-10 }}</ref>但[[美國聯邦第十巡迴上訴法院]]於2006年8月17日裁定，維持FDA的最終規則，宣佈所有含麻黃鹼生物鹼的膳食補充劑均被摻假，因此在美國銷售屬於非法。<ref>{{cite court |litigants= Nutraceutical Corporation; Solaray, Inc. Plaintiffs-Appellees vs. Andrew Von Eschenbach, Acting Commissioner, US.. Food and Drug Administration; United States Food and Drug Administration; Michael O. Leavitt, Secretary of the Department of Health and Human Services; Department of Health and Human Services; United States of America |opinion= We find that the FDA correctly followed the congressional directive to analyze the risks and benefits of EDS in determining that there is no dosage level of EDS acceptable for the market. |court= United States Court of Appeals Tenth Circuit |date= August 17, 2006|access-date= 2007-02-16 | url= https://web.archive.org/web/20080921084346/http://www.ck10.uscourts.gov/opinions/05/05-4151.pdf }}{{dead link|date=October 2023}}</ref>此外，麻黃鹼被[[國家大學體育協會]]、[[美國職業棒球大聯盟]]、[[國家美式足球聯盟]]和[[美國職業高爾夫球員協會]]禁用。<ref>{{cite web |url= http://www.drugfreesport.com/drug-resources/faq.asp |title=Sport Drug Testing – Drug Programs & Policy – Athletics |access-date= 2011-03-21 |url-status=dead |archive-url=https://web.archive.org/web/20110210135236/http://www.drugfreesport.com/drug-resources/faq.asp |archive-date=2011-02-10 }}</ref>然而，麻黃鹼在膳食補充劑以外的許多應用中仍然合法。目前對其採購受到限制和監控，具體情況因州而異。

[[美國眾議院]]於2005年通過{{le|打擊安非他命流行法案|Combat Methamphetamine Epidemic Act of 2005 }}，作為《[[美國愛國者法]]》的更新修正案。此法案於2006年3月6日由[[喬治·沃克·布希]]（小布希）總統簽署成為法律，其中修訂[[美國法典]] (21 USC 830)中有關銷售含有麻黃鹼和密切相關的偽麻黃鹼的產品。這兩種物質都被用作生產甲基安非他命的前體，為阻止這類非法使用，聯邦法對銷售此類產品的商家提出以下要求：

*所有購買均須留下記錄，標明買方的姓名和地址，記錄保存兩年
*需要驗證所有購買者的身份證明
*對收集的個人資訊提供的保護和揭露方法
*向[[美國司法部長]]報告任何可疑付款或受管制產品失踪的情況
*受管制產品中的非液體劑型只能以單位劑量泡罩包裝出售
*受管制產品應在櫃檯後面或上鎖的櫃子中保存，以管制接觸
*每日向單一購買者銷售的受管制產品不得超過3.6克，（不論交易數量）
*每月向單一購買者銷售的受管制產品中的偽麻黃鹼含量不得超過9克

法案對採郵購購買方式有類似的規定，但每月銷售限量為7.5克。

含有麻黃鹼的純草藥或茶在美國仍可合法銷售。法律限制/禁止其作為膳食補充劑（片劑）或作為其他產品（如減肥藥）的成分/添加劑出售。

====澳大利亞====
麻黃鹼和所有包包含它的麻黃屬物種均被視為《[[藥物和毒物的統一調度標準]]》中附表4物質。附表4藥物被視為純[[處方藥]]物或處方動物藥物 - 只有經州或地區允許的人才能使用或供應的物質，並且應根據前述《調度標準準》由藥劑師按照處方箋提供。

====南非====
在南非，麻黃鹼於2008年5月27日移至《1965年藥品及相關物質法》附表6中，<ref>{{cite web |url=http://www.doh.gov.za/docs/pr/2008/pr0527.html |title=Rescheduling of Medicines that Contain Ephedrine |access-date=2009-04-18 |url-status=dead |archive-url= https://web.archive.org/web/20090628091843/http://www.doh.gov.za/docs/pr/2008/pr0527.html |archive-date=2009-06-28 }}</ref>使得純麻黃鹼片劑僅能作為處方藥。每片含麻黃鹼最多30毫克的片劑與其他藥物組合仍可作為非處方藥使用（附表1和2），用於治療鼻竇、感冒和流行性感冒。

====德國====
麻黃鹼於2001年之前可在德國的藥房中自由購買。之後由於購買均非作治療用途，因而受到管制。同樣的，購買麻黃也只能憑處方從事。自2006年4月起，所有含有麻黃鹼的產品，包括植物部分，都必須憑處方箋才能購買。<ref>[http://www.buzer.de/gesetz/7048/index.htm ''Verordnung zur Neuordnung der Verschreibungspflicht von Arzneimitteln (AMVVNV).''] {{webarchive |url= https://web.archive.org/web/20140517122414/http://www.buzer.de/gesetz/7048/index.htm |date=2014-05-17 }} V. v. 21. Dezember 2005 BGBl. I S. 3632; Geltung ab 1. Januar 2006.</ref>

==來源==
傳統上麻黃鹼是從植物麻黃和麻黃屬的其他成員中萃取。麻黃鹼和中藥原料在中國大量生產。截至2007年，中國各公司每年從3萬噸麻黃（約為中藥用量的十倍）中生產價值1,300萬美元的麻黃素作出口用途。<ref name=Chen>{{cite web | vauthors = Long C |url= http://www.chinadialogue.net/article/show/single/en/692-Chinese-medicine-s-great-waste-of-resources |title=Chinese medicine's great waste of resources |date= 2007-01-15 |access-date= 2016-05-09 |url-status=live |archive-url=https://web.archive.org/web/20160530231517/https://www.chinadialogue.net/article/show/single/en/692-Chinese-medicine-s-great-waste-of-resources |archive-date= 2016-05-30 }}</ref>

有採用[[苯甲醛]]、[[肉桂酸]]和 1-苯基丙酮等進行化學合成麻黃鹼及偽麻黃鹼的報導。<ref>{{cite journal |last1=Zhu |first1=Binling |last2= Conlan |first2=Xavier |date=July 2020 |title= Case studies on illegal production of ephedrine/pseudoephedrine within Fujian China|url=https://www.sciencedirect.com/science/article/abs/pii/S0379073820301882 |journal= Forensic Science International|volume=312 |issue= |pages= |doi= 10.1016/j.forsciint.2020.110326|access-date=2024-09-02}}</ref>

[[File:Ephedrine biosynthesis.svg |thumb|400px|right|麻黃鹼的假設生物合成途徑 - 徑涉及左旋-苯丙氨酸和丙酮酸兩種化合物的轉化。<ref name="Hertweck">{{cite journal | vauthors = Hertweck C, Jarvis AP, Xiang L, Moore BS, Oldham NJ | title = A mechanism of benzoic acid biosynthesis in plants and bacteria that mirrors fatty acid beta-oxidation | journal = ChemBioChem | volume = 2 | issue = 10 | pages = 784–6 | date = October 2001 | pmid = 11948863 | doi = 10.1002/1439-7633(20011001)2:10<784::AID-CBIC784>3.0.CO;2-K | s2cid = 28159196 }}<!--|access-date = 2015-06-10--></ref><ref name="Grue-Sorensen 3714–3715">{{Cite journal |title= Biosynthesis of ephedrine |journal= Journal of the American Chemical Society |date= May 1, 1988 |issn= 0002-7863 |pages= 3714–3715 |volume= 110 |issue= 11 |doi= 10.1021/ja00219a086 | vauthors = Grue-Sorensen G, Spenser ID }}</ref>]]

也有研究人員探討以生物合成途經生產麻黃鹼的方式。<ref name="sciencedirect.com">{{cite journal |title= Participation of C6-C1 unit in the biosynthesis of ephedrine in Ephedra |doi= 10.1016/0031-9422(73)80499-6 |volume=12 |issue=12 |journal= Phytochemistry |pages= 2877–2882 |year= 1973 | vauthors = Yamasaki K, Tamaki T, Uzawa S, Sankawa U, Shibata S |bibcode= 1973PChem..12.2877Y }}</ref><ref name="Hertweck"/><ref name="Grue-Sorensen 3714–3715"/>








嚴重副作用有乳酸性酸中毒、{{le|肝毒性|Hepatotoxicity}}、[[肝腫大]]和[[脂肪肝]]。<ref name="Baraclude FDA label" />


化驗室檢查可能顯示使用者的[[谷丙转氨酶|麩丙轉胺酶]] (ALT) 升高、[[血尿]]、{{le|糖尿|Glycosuria}}和[[脂酶]]升高。<ref name="Baraclude FDA label" />建議使用者定期進行肝功能和血液學監測。<ref name="Baraclude FDA label" />


==作用機轉==
恩替卡韋是一種{{le|核苷類似物|Nucleoside analogue}}，<ref name="pmid17125436">{{cite journal | vauthors = Sims KA, Woodland AM | title = Entecavir: a new nucleoside analog for the treatment of chronic hepatitis B infection | journal = Pharmacotherapy | volume = 26 | issue = 12 | pages = 1745–1757 | date = December 2006 | pmid = 17125436 | doi = 10.1592/phco.26.12.1745 | s2cid = 13149070 | doi-access = free }}</ref>或更具體而言，是一種[[脫氧鳥苷]]類似物，屬於一類{{le|碳環核苷|Carbocyclic nucleoside}}，在{{le|病毒複製|Viral replication}}過程中將反轉錄、[[DNA複製]]和[[轉錄]]抑制住。其他的[[核苷]]和核苷酸類似物有拉米夫定、[[替比夫定]]、[[阿德福韋]]和[[替諾福韋]]。


恩替卡韋可透過降低B型肝炎病毒繁殖和感染新細胞的能力來減少血液中B型肝炎病毒的數量。<ref>{{cite web|url=https://www.drugs.com/cdi/entecavir.html|title=Entecavir: Indications, Side Effects, Warnings - Drugs.com|website=www.drugs.com|access-date= 2016-11-07|url-status=live|archive-url=https://web.archive.org/web/20161107161241/https://www.drugs.com/cdi/entecavir.html|archive-date=2016-11-07}}</ref>


==給藥==
恩替卡韋是供口服使用的片劑或溶液。使用劑量取決於人的體重。<ref name="Baraclude FDA label" />建議2歲以上、體重不超過30公斤的兒童方可使用，在飯前或飯後至少2小時空腹時服用，且儘量在每天同一時間服用。 2歲以下兒童不宜使用。也建議腎功能下降的人要調整劑量。<ref name="Baraclude FDA label" />


==藥物發展歷史==
*1992年：此藥物最初源自施貴寶（[[必治妥施貴寶]]藥廠的前身之一）開發抗皰疹病毒計畫（藥物代號SQ-34676）中的一項。<ref>{{cite journal | vauthors=Slusarchyk, WA, Field AK, Greytok JA, Taunk P, Tooumari AV, Young MG, Zahler R | title=4-Hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl purines and pyrimidines, a new class of anti-herpesvirus agents | journal=Antiviral Research | volume=17 | year=1992 | doi=10.1016/0166-3542(92)90200-o | page=98}}</ref>
*1997年：比治妥施貴寶（簡稱BMS）開發的一種抗病毒核苷類似物（藥物代號BMS 200475），在細胞株中顯示出對B型肝炎病毒、HSV-1（一種DNA病毒，常見於引起唇皰疹）、HCMV（一種DNA病毒，屬於β型皰疹病毒）、VZV（一種DNA病毒，引起水痘和帶狀皰疹）具有活性，而對愛滋病毒或[[流行性感冒]]病毒幾乎沒活性。<ref name="Bisacch_1997">{{cite journal | vauthors = Bisacchi GS, Chao ST, Bachard C, Daris JP, Innaimo SF, Jacobs JA, Kocy O, Lapointe P, Martel A, Merchant Z, Slusarchyk WA, Sundeen JE, Young MG, Colonno R, Zahler R | year = 1997 | title = BMS-200475, a novel carbocyclic 29-deoxyguanosine analog with potent and selective antihepatitis B virus activity in vitro | journal = Bioorganic & Medicinal Chemistry Letters | volume = 7 | issue = 2| pages = 127–132 | doi=10.1016/s0960-894x(96)00594-x }}</ref>
*BMS 200475及其衍生化合物在HepG2.2.15細胞株（一種經過基因工程改造的肝癌細胞株）中顯示出對B型肝炎病毒具優越活性，促使研究人員進一步研究。<ref name="Bisacch_1997" />
*由於該化合物是[[鳥嘌呤]]核苷類似物，因此被證明是B型肝炎病毒更具選擇性的有效抑制劑。<ref>{{cite journal | vauthors = Innaimo SF, Seifer M, Bisacchi GS, Standring DN, Zahler R, Colonno RJ | title = Identification of BMS-200475 as a potent and selective inhibitor of hepatitis B virus | journal = Antimicrobial Agents and Chemotherapy | volume = 41 | issue = 7 | pages = 1444–1448 | date = July 1997 | pmid = 9210663 | pmc = 163937 | doi = 10.1128/AAC.41.7.1444 }}</ref>
*1998年：該化合物與多種核苷類似物 - {{le|三磷酸酯|Trimethyl phosphate}}（NAs-TP）相比，在[[in vitro]]（體外）證明對肝炎病毒聚合酶具抑制作用。<ref>{{cite journal | vauthors = Seifer M, Hamatake RK, Colonno RJ, Standring DN | title = In vitro inhibition of hepadnavirus polymerases by the triphosphates of BMS-200475 and lobucavir | journal = Antimicrobial Agents and Chemotherapy | volume = 42 | issue = 12 | pages = 3200–3208 | date = December 1998 | pmid = 9835515 | pmc = 106023 | doi = 10.1128/AAC.42.12.3200 }}</ref>
*代謝研究顯示該化合物更容易被磷酸化，而轉化為具有生物活性的三磷酸形式。<ref>{{cite journal | vauthors = Yamanaka G, Wilson T, Innaimo S, Bisacchi GS, Egli P, Rinehart JK, Zahler R, Colonno RJ | title = Metabolic studies on BMS-200475, a new antiviral compound active against hepatitis B virus | journal = Antimicrobial Agents and Chemotherapy | volume = 43 | issue = 1 | pages = 190–193 | date = January 1999 | pmid = 9869593 | pmc = 89048 | doi = 10.1128/AAC.43.1.190 | doi-access = free }}</ref>
*對[[美洲旱獺|美洲土撥鼠]]慢性B型肝炎模型進行3年的治療，顯示出該化合物持續的抗病毒和延長壽命的功效，且未檢測到耐藥性出現。<ref>{{cite journal | vauthors = Colonno RJ, Genovesi EV, Medina I, Lamb L, Durham SK, Huang ML, Corey L, Littlejohn M, Locarnini S, Tennant BC, Rose B, Clark JM | title = Long-term entecavir treatment results in sustained antiviral efficacy and prolonged life span in the woodchuck model of chronic hepatitis infection | journal = The Journal of Infectious Diseases | volume = 184 | issue = 10 | pages = 1236–1245 | date = November 2001 | pmid = 11679911 | doi = 10.1086/324003 | doi-access = free }}</ref>
*體外研究該化合物對拉米夫定耐藥B型肝炎病毒具抑制作用。<ref>{{cite journal | vauthors = Levine S, Hernandez D, Yamanaka G, Zhang S, Rose R, Weinheimer S, Colonno RJ | title = Efficacies of entecavir against lamivudine-resistant hepatitis B virus replication and recombinant polymerases in vitro | journal = Antimicrobial Agents and Chemotherapy | volume = 46 | issue = 8 | pages = 2525–2532 | date = August 2002 | pmid = 12121928 | pmc = 127388 | doi = 10.1128/aac.46.8.2525-2532.2002 }}</ref>
*該化合物在體內對HBeAg（B型肝炎病毒表面抗原）陽性及陰性患者均較拉米夫定具有更優越的活性<ref>{{cite journal | vauthors = Chang TT, Gish RG, de Man R, Gadano A, Sollano J, Chao YC, Lok AS, Han KH, Goodman Z, Zhu J, Cross A, DeHertogh D, Wilber R, Colonno R, Apelian D | title = A comparison of entecavir and lamivudine for HBeAg-positive chronic hepatitis B | journal = The New England Journal of Medicine | volume = 354 | issue = 10 | pages = 1001–1010 | date = March 2006 | pmid = 16525137 | doi = 10.1056/nejmoa051285 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Lai CL, Shouval D, Lok AS, Chang TT, Cheinquer H, Goodman Z, DeHertogh D, Wilber R, Zink RC, Cross A, Colonno R, Fernandes L | title = Entecavir versus lamivudine for patients with HBeAg-negative chronic hepatitis B | journal = The New England Journal of Medicine | volume = 354 | issue = 10 | pages = 1011–1020 | date = March 2006 | pmid = 16525138 | doi = 10.1056/NEJMoa051287 | doi-access = free | hdl = 10722/45018 | hdl-access = free }}</ref>
*該化合物對使用拉米夫定治療無效的B型肝炎患者具有較佳的治療效果。<ref>{{cite journal | vauthors = Sherman M, Yurdaydin C, Sollano J, Silva M, Liaw YF, Cianciara J, Boron-Kaczmarska A, Martin P, Goodman Z, Colonno R, Cross A, Denisky G, Kreter B, Hindes R | title = Entecavir for treatment of lamivudine-refractory, HBeAg-positive chronic hepatitis B | journal = Gastroenterology | volume = 130 | issue = 7 | pages = 2039–2049 | date = June 2006 | pmid = 16762627 | doi = 10.1053/j.gastro.2006.04.007 | doi-access = free }}</ref>
*恩替卡韋於2005年3月獲得FDA批准用作醫療用途。<ref>{{cite web | title=Drug Approval Package: Baraclude (Entecavir) NDA #021797 & 021798 | website=U.S. [[Food and Drug Administration]] (FDA) | date=2011-12-28 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21797_21798_BaracludeTOC.cfm | access-date=2021-01-24 | archive-date=2013-03-24 | archive-url=https://web.archive.org/web/20130324094415/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21797_21798_BaracludeTOC.cfm | url-status=live }}</ref>


===專利資訊===
比治妥施貴寶是恩替卡韋（商品名稱Baraclude）在[[美國]]和[[加拿大]]的原始專利持有者。Baraclude的專利於2015年到期。<ref>{{cite web|url=http://www.accessdata.fda.gov/scripts/cder/ob/docs/patexclnew.cfm?Appl_No=021797&Product_No=001&table1=OB_Rx|title=Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations|website=U.S. [[Food and Drug Administration]] (FDA)|archive-url=https://web.archive.org/web/20160304084741/http://www.accessdata.fda.gov/scripts/cder/ob/docs/patexclnew.cfm?Appl_No=021797&Product_No=001&table1=OB_Rx|archive-date=2016-03-04|access-date=2015-08-29|url-status=dead}}</ref><ref>{{cite web|url=http://www.accessdata.fda.gov/scripts/cder/ob/patent_info.cfm?Product_No=001&Appl_No=021798&Appl_type=N|title=Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations|website=U.S. [[Food and Drug Administration]] (FDA)|access-date=2016-11-14|url-status=unfit|archive-url=https://web.archive.org/web/20161115140215/http://www.accessdata.fda.gov/scripts/cder/ob/patent_info.cfm?Product_No=001&Appl_No=021798&Appl_type=N|archive-date=2016-11-15}}</ref>此藥物專利全是比治妥施貴寶（專利所有者）和[[梯瓦]]製藥(美國)（通用名藥物製造商）在美國發生訴訟的焦點。這起訴訟經由[[美國聯邦巡迴區上訴法院]]的審理，最終因該專利所涉及的技術在當時已屬眾所周知，法院認定其為顯而易見，並於2014年6月宣布專利無效，此判決在製藥產業引發不小關注。


==參考文獻==
梯瓦製藥(美國)於2014年8月獲得FDA批准，將Bararude0.5毫克和1毫克片劑的通用名藥物上市，<ref>{{cite web|url=http://www.accessdata.fda.gov/scripts/cder/ob/docs/obdetail.cfm?Appl_No=202122&TABLE1=OB_Rx|title=Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations|website=U.S. [[Food and Drug Administration]] (FDA)|at=Search results from the "OB_Rx" table for query on "202122."|archive-url=https://web.archive.org/web/20151222125427/http://www.accessdata.fda.gov/scripts/cder/ob/docs/obdetail.cfm?Appl_No=202122&TABLE1=OB_Rx|archive-date=2015-12-22|access-date= 2015-08-29|url-status=dead}}</ref>印度藥廠{{le|Hetero Drugs|Hetero Drugs}}生產的通用名藥物於2015年8月21日獲得FDA批准上市，<ref>{{cite web|url=http://www.accessdata.fda.gov/scripts/cder/ob/docs/obdetail.cfm?Appl_No=205740&TABLE1=OB_Rx|title=Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations|website=U.S. [[Food and Drug Administration]] (FDA)|at=Search results from the "OB_Rx" table for query on "205740."|archive-url=https://web.archive.org/web/20160304060955/http://www.accessdata.fda.gov/scripts/cder/ob/docs/obdetail.cfm?Appl_No=205740&TABLE1=OB_Rx|archive-date=4 March 2016|access-date=2015-08-29|url-status=dead}}</ref>另一大型印度藥廠{{le|Aurobindo Pharma|Aurobindo Pharma}}生產的通用名藥物於2015年8月26日獲得FDA批准上市。<ref>{{cite web|url=http://www.accessdata.fda.gov/scripts/cder/ob/docs/obdetail.cfm?Appl_No=206217&TABLE1=OB_Rx|title=Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations|website=U.S. [[Food and Drug Administration]] (FDA)|at=Search results from the "OB_Rx" table for query on "206217."|archive-url=https://web.archive.org/web/20160304053459/http://www.accessdata.fda.gov/scripts/cder/ob/docs/obdetail.cfm?Appl_No=206217&TABLE1=OB_Rx|archive-date=2016-03-04|access-date=2015-08-29|url-status=dead}}</ref>
{{Reflist|2}}


== 參考文獻 ==
==外部連結==
{{Commons category|L-Ephedrine}}
{{reflist|2}}


{{模板:抗DNA病毒藥物}}
{{模板:散瞳藥和睫狀肌麻痹藥}}
{{Nasal preparations}}
{{Portal bar | Medicine | Viruses}}
{{Monoamine releasing agents}}
{{Phenethylamines}}
{{Portal bar | Medicine}}
{{Authority control}}
{{Authority control}}


{{draft categories|
{{draft categories|
[[分類:核苷類似物逆轉錄酶抑制劑]]
[[分類:苯丙胺類生物鹼]]
[[分類:嘌呤]]
[[分類:降食慾劑]]
[[分類:肝毒素]]
[[分類:抗肥胖藥]]
[[分類:強心劑]]
[[分類:中國發明]]
[[分類:解充血藥]]
[[分類:作用於心血管系統的藥物]]
[[分類:作用於神經系統的藥物]]
[[分類:體育用藥]]
[[分類:對映純藥物]]
[[分類:安樂藥]]
[[分類:漢朝]]
[[分類:甲基苯丙胺]]
[[分類:去甲腎上腺素釋放劑]]
[[分類:苯乙醇胺]]
[[分類:興奮劑]]
[[分類:苯丙胺類]]
[[分類:擬交感神經藥]]
[[分類:中醫e]]
[[分類:世界反興奮劑機構禁用物質]]
[[分類:世界衛生組織基本藥物]]
[[分類:世界衛生組織基本藥物]]
[[分類:RTT]]
[[分類:RTT]]
[[Category:Antihypotensive agents]]
[[分類:環戊基化合物]]
[[Category:Ergogenic aids]]
[[分類:烯烴衍生物]]
[[分類:羥甲基化合物]]
[[Category:Drugs developed by Bristol Myers Squibb]]
}}
}}

2024年9月2日 (一) 08:35的版本

维基百科中的醫學内容仅供参考，並不能視作專業意見。如需獲取醫療幫助或意見，请咨询专业人士。詳見醫學聲明。
ThomasYehYeh/沙盒/伊朗罪案
Chemical structure of the (1R,2S)-ephedrine molecule
Ball-and-stick model of the (1R,2S)-ephedrine molecule
(−)-(1R,2S)-ephedrine chemical structure (top) and ball-and-stick model (bottom)
臨床資料
读音聆聽i/ɪˈfɛdrɪn/ or /ˈɛfɪdriːn/
商品名（英语：Drug nomenclature）Akovaz、Corphedra、Emerphed及其他
其他名稱(−)-Ephedrine; (1R,2S)-Ephedrine; (1R,2S)-β-Hydroxy-N-methylamphetamine; (1R,2S)-β-Hydroxy-N-methyl-α-methyl-β-phenethylamine
AHFS/Drugs.comEphedrine: Monograph
HCl: Monograph
Sulfate: Monograph
懷孕分級
  • 澳: A
给药途径口服給藥、靜脈注射 (IV)、肌肉注射 (IM)及皮下注射 (SC)
ATC碼
法律規範狀態
法律規範
藥物動力學數據
生物利用度88%[5]
血漿蛋白結合率~24–29% (其中5%至10%與人類血清白蛋白（英语：Human serum albumin）結合)[6][7][8]
药物代谢大部分未被代謝[5][9]
代謝產物• 苯丙醇胺[5][9]
藥效起始時間（英语：Onset of action）IV (幾秒內), IM (10-20分鐘), 口服 (15-60分鐘)[10]
生物半衰期6 hours[5]
作用時間IV/IM (60分鐘), 口服 (2-4小時)
排泄途徑主要經尿液 (有60%為原形)[5]
识别信息
  • (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
CAS号299-42-3（
50-98-6 (hydrochloride)）  checkY
134-72-5  checkY
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
化学信息
化学式C10H15NO
摩尔质量165.24 g·mol−1
3D模型（JSmol（英语：JSmol））
  • C[C@@H]([C@@H](C1=CC=CC=C1)O)NC
  • InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1 checkY
  • Key:KWGRBVOPPLSCSI-WPRPVWTQSA-N checkY

麻黃鹼（英語：ephedrine是一種中樞神經系統 (簡稱CNS) 興奮劑，常用於預防麻醉期間的低血壓。[10] 它也被用於治療氣喘、發作性嗜睡病和肥胖症，但均非首選藥物。[10]它在治療鼻塞的益處尚不清楚。給藥方式有口服、肌肉注射、靜脈注射或皮下注射。[10]靜脈注射後發生效用最快，肌肉注射將需20分鐘，口服則需要1小時才能發揮作用。[10]注射給藥時，其效力持續時間約為一小時，而口服時，其效力持續時間可達四小時。[10]

使用後常見的副作用有睡眠困難、焦慮、頭痛、幻覺、高血壓、心跳過速、食慾不振和尿瀦留。[10]嚴重的副作用有中風和心肌梗塞。[10]雖然個體於懷孕期間使用可能對於胎兒安全，但在該群體中的研究很少。[12][13]不建議在母乳哺育期間使用以確保嬰兒安全。[13]麻黃鹼通過誘導正腎上腺素的釋放而起作用，因此間接激活α腎上腺素受體和β腎上腺素受體。取代安非他命（英语：Substituted amphetamine）從化學角度來看，麻黃鹼是一種取代安非他命（英语：Substituted amphetamine），並且是 (1R,2S)-β-羥基-N-甲基安非他命的對映異構體。取代安非他命（英语：Substituted amphetamine）

麻黃鹼於1885年首次被成功萃取，並於1926年進入商業用途。[14][15]它已被納入世界衛生組織基本藥物標準清單之中。[16]市面上有其通用名藥物流通。[10]它通常是麻黃屬植物中常見的物質。美國法律不允許含有麻黃鹼的非處方膳食補充劑販售，[10]但用於中藥學的補充劑除外，用"má huáng（麻黃）"指出其中含有此種物質。[10][17]

醫療用途

硫酸鹽麻黃鹼（1932年）、麻黃鹼合成物（1932年）及Swan-Myers藥廠出品的66號麻黃鹼吸入劑（約1940年）。

麻黃鹼是一種非兒茶酚胺擬交感神經藥，其心血管作用與腎上腺素相似：可升高血壓、心跳和心肌收縮力。麻黃鹼與偽麻黃鹼一樣，是一種支氣管擴張藥，但偽麻黃鹼的作用要小很多。[18][19]

麻黃鹼可以減少暈動病，但它主要用於減少其他用於暈動病的藥物的鎮靜作用。[20][21]

麻黃鹼也被發現對幼兒期先天性肌無力症候群（英语：Congenital myasthenic syndrome）具有快速且持久的反應性，甚至對具有新型COLQ基因（英语：COLQ）突變的成年人（會導致重症肌無力）也具有快速且持久的反應性。[22]

經由靜脈快速推注給藥後，重新給藥時通常需要增加劑量以抵消急速耐藥性的發生，這是由於持續刺激導致個體兒茶酚胺耗竭所致，而產生藥物耐受性。[18]

減肥

麻黃鹼因尤其可降低體脂肪，可達到短期適度減肥的目的，[23]但此藥物的長期影響尚不清楚。[24]在小鼠身上的實驗，已知麻黃鹼會刺激棕色脂肪組織中的產熱作用，但由於成年人只有少量棕色脂肪，因此推測產熱主要發生在骨骼肌中。麻黃鹼可降低胃排空的速度。咖啡因和茶鹼等黃嘌呤與麻黃鹼在減肥方面具協同作用，而導致商家創建及行銷三者複合的產品。[25]其中一種被稱為ECA stack（英语：ECA stack），含有麻黃鹼、咖啡因和阿斯匹靈，是參與健美比賽者在賽前減少體內脂肪常用的補充劑。 [26]於2021年所作的一項系統性回顧發現個體使用麻黃鹼可比使用安慰劑者減輕2公斤的體重（4.4磅），提高心率，降低低密度脂蛋白水平，提高高密度脂蛋白水平，但血壓方面無統計學上的顯著差異。[27]

市售配方

麻黃鹼在美國是以靜脈注射液形式的處方藥銷售，品牌名稱有Akovaz、Corphedra、Emerphed和 Rezipres以及通用名藥物。[28][29]也有非處方藥以12.5和 25毫克口服片劑形式，用作支氣管擴張劑和用作舒緩鼻塞藥（英语：decongestant）的0.5%濃度鼻噴劑。[29]麻黃鹼也可與癒創甘油醚組成複方的口服片劑和藥水。[29]麻黃鹼在藥品中通常以鹽酸鹽或硫酸鹽的形式存在，以增加其穩定性和溶解度。[28][29]

禁忌症

麻黃鹼不可與某些抗憂鬱劑（即去甲腎上腺素-多巴胺再吸收抑制劑（NDRI））一起使用，因為這會增加因血清正腎上腺素（又稱去甲腎上腺素）水平過高而可能導致一系列併發症。

安非他酮是一種抗憂鬱藥，具有與麻黃鹼相似的苯丙胺樣結構，是一種NDRI。其作用更類似安非他命，而非氟西汀，因為它的主要治療作用涉及正腎上腺素，在較小程度上涉及多巴胺，但它也會從突觸前裂釋放一些血清素。它不應與麻黃鹼一起使用，因為可能會增加副作用的可能性。

麻黃鹼應謹慎用於以下患者：[30]

個體於懷孕期間使用麻黃鹼可能對胎兒造成潛在風險，因此一般不建議使用。 只有在病情嚴重，且其他藥物無法作用的情況下，才可能在醫師的評估下謹慎進行。[30]

副作用

麻黃鹼是一種有潛在危險性的天然化合物，截至2004年，美國食品藥物管理局（FDA）已收到超過18,000份有關使用後出現不良反應的報告。[31]

全身給藥（例如注射或口服方式）的藥物不良反應（ADR）較局部給藥（如鼻腔噴藥）更為常見。與麻黃鹼治療相關的不良反應包含有：[32]

過量

使用過量的麻黃鹼會引起血壓快速上升。個體發生使用過量的情況時，須時時檢測血壓，必要時可注射型降血壓藥處理，如果有呼吸急促或出現發紺，須確保患者氣道暢通並提供機械換氣。[33]

藥物交互作用

麻黃鹼與單胺氧化酶抑制劑（MAOIs）如苯乙肼（英语：Phenelzine）和反苯環丙胺一起使用可能會導致高血壓危機（英语：Hypertension crisis）。[34]

藥理學

藥效學

麻黃鹼是一種擬交感神經藥，作用於部分交感神經系統 (SNS)。其主要作用機制依賴於其間接刺激腎上腺素受體系統，通過增加正腎上腺素在突觸後α和β受體上的活性。[35]與α受體直接相互作用的可能性不大，但仍有爭議。[36][19][37][38]左旋麻黃鹼，特別是其立體異構體去甲偽麻黃鹼（也存在於麻黃鹼中）具有間接擬交感神經作用，並且由於其能夠穿過血腦屏障，因此它是一種類似於安非他命的中樞神經系統興奮劑，但不太明顯，因為它在大腦中釋放正腎上腺素和多巴胺，與安非他命的釋放位置不同。[39]

藥物動力學

吸收

麻黃鹼的口服劑生物利用度為88%。口服後15至60分鐘開始作用，肌肉注射後10至20分鐘開始作用，靜脈輸注後則在數秒內開始作用。[10]

分佈

此藥物的血漿蛋白結合率約為24%至29%，其中5%至10%與人類血清白蛋白（英语：Human serum albumin）結合。[6][7][8]

代謝

大部分麻黃鹼不會被代謝。正腎上腺素（苯丙醇胺）是麻黃鹼經由N-去甲基化形成的活性代謝物。[5][9]口服劑的麻黃鹼中約8%至20%去甲基化為正腎上腺素，約4%至13%氧化脫氨為苯甲酸，一小部分轉化為1,2-二羥基-1-苯基丙烷。[9]

消除

麻黃鹼主要經由尿液排出體外，其中60%（範圍 53-79%）以原形排出。[9]

麻黃鹼的生物半衰期為6小時。[5]口服作用時間為2至4小時，靜脈或肌肉注射作用持續時間為60分鐘。

化學

麻黃鹼是一種擬交感神經藥和取代安非他命。它的分子結構與苯丙醇胺、甲基安非他命和腎上腺素相似。從化學角度來看，它是一種具有苯乙胺骨架的生物鹼，存在於麻黃屬的各種植物中。它主要透過增加腎上腺素受體上正腎上腺素的活性來發揮作用。[28][33]此藥物通常以鹽酸鹽或硫酸鹽的形式銷售。

鹽酸鹽麻黃鹼的熔點為187−188°C。[9]

麻黃鹼的四種立體異構體。

體液檢測

麻黃鹼可在人體血液、血漿或尿液中進行定量檢測，以監測運動員可能的濫用，確認中毒診斷或協助法醫進行死因調查。許多針對安非他命的商業免疫分析篩檢與麻黃鹼明顯發生交叉反應，但利用色層分析法可輕鬆將麻黃鹼和其他苯乙胺衍生物區分。服用該藥物患者的血液或血漿麻黃鹼濃度通常在20-200維克/升（μg/L）的範圍，濫用者或中毒患者的在300-3,000維克/升的範圍，在急性致命過量用藥情況下的在3-20毫克/升的範圍。目前世界反運動禁藥機構(WADA) 對運動員尿液中麻黃鹼設定的底線標準為10維克/升。[40][41][42][43]

歷史

亞洲

中醫學將天然形式的麻黃鹼稱為“麻黃（máhuáng）”，自漢朝（公元前206年至公元220年）起就被作為一種平緩氣喘劑和興奮劑來使用。[44]傳統中醫在過去幾個世紀均將麻黃用來治療氣喘和支氣管炎。[45]

日本有機化學家永井長吉（英语：Nagai Nagayoshi）於1885年根據其對日本和中國傳統草藥的研究，首先以化學合成方式造出麻黃鹼。 中國以工業化方式生產麻黃鹼始於1920年代，由默克製藥以麻黃素的名義推廣和銷售這種藥物。 中國於1926年至1928年的兩年間向西方出口的麻黃素從4噸增加到216噸。[46]

西醫

麻黃鹼於1926年首次在美國被引入醫療用途。[31]

美國Vicks製藥於1948年推出一款含有硫酸麻黃鹼作為活性成分的滴鼻劑上市（商品名Vatronol），可快速緩解鼻充血，此產品現已停止銷售。

社會與文化

休閒用途

麻黃鹼片劑

麻黃鹼一種是苯乙胺，其化學結構與安非他命類似，是一種甲基安非他命類似物，具有甲基安非他命結構，且β位有羥基。由於麻黃鹼的結構與甲基安非他命相似，因此可透過化學還原除去麻黃鹼的羥基來製造甲基安非他命；使得麻黃鹼成為非法製造甲基安非他命備受追捧的前驅物。

將麻黃鹼還原為甲基安非他命的最流行方法與伯奇還原反應類似。第二種最受歡迎的方法是使用紅磷和碘與麻黃鹼反應。此外，麻黃鹼可透過簡單的氧化合成甲卡西酮（被《精神藥物公約》和受管制物質法案列為表一類受管制物質）。因此麻黃鹼被《聯合國禁止非法販運麻醉藥品和精神藥物公約》列為表一類前體藥物。

運動和體能活動用途

麻黃鹼經常被用作運動和體能活動中的表現增強物質。[36][47][48][49]它可以提高心率、血壓和心肌收縮力，並作為一種興奮劑。[36]麻黃鹼通常與咖啡因一起用於增強體能表現。[48][49]

其他用途

在化學合成中，麻黃鹼被大量用於手性助劑的用途。[50]

麻黃鹼作為手性助劑用途。

在合成沙奎那韋（一種抗反轉錄病毒藥物）的過程中，為分離出具有特定結構的半酸分子，科學家會將它與左旋麻黃鹼結合形成鹽。這個鹽的形成有助於將需要的半酸從其他物質中分離出來。

法律地位

加拿大

加拿大衛生部於2002年1月發佈自願召回令，將所有每劑含量超過8毫克的麻黃鹼產品、所有麻黃鹼與其他興奮劑（例如咖啡因）的組合以及所有用於減肥或健美適應症的麻黃鹼產品收回，理由是存在嚴重健康風險。[51] Ephedrine is still sold as an oral nasal decongestant[52]麻黃鹼仍以口服舒緩鼻塞藥，以8毫克片劑的形式作為天然保健品出售，每包的麻黃鹼含量限量為0.4克（400毫克），這是加拿大《管制藥物和物質法》規定的成分上限，麻黃鹼被認為是A類前驅藥物。[53]

美國

FDA於1997年提出一項關於麻黃（可萃取麻黃鹼的草藥）的法規，將麻黃劑量限制為8毫克（活性麻黃鹼），每天用量不超過24毫克。[54]該擬議規則於2000年被撤回，部分原因是"該機構所提出的特定膳食成分含量和產品使用期限的依據，受到廣泛質疑。”[55]FDA於2004年對非哮喘、感冒、過敏、其他疾病或傳統亞洲使用的麻黃鹼生物鹼發佈禁令。[56]美國猶他聯邦地區法院於2005年4月14日裁定FDA沒適當的證據表明低劑量麻黃鹼生物鹼實際上是不安全的，[57]但美國聯邦第十巡迴上訴法院於2006年8月17日裁定，維持FDA的最終規則，宣佈所有含麻黃鹼生物鹼的膳食補充劑均被摻假，因此在美國銷售屬於非法。[58]此外，麻黃鹼被國家大學體育協會、美國職業棒球大聯盟、國家美式足球聯盟和美國職業高爾夫球員協會禁用。[59]然而，麻黃鹼在膳食補充劑以外的許多應用中仍然合法。目前對其採購受到限制和監控，具體情況因州而異。

美國眾議院於2005年通過打擊安非他命流行法案（英语：Combat Methamphetamine Epidemic Act of 2005），作為《美國愛國者法》的更新修正案。此法案於2006年3月6日由喬治·沃克·布希（小布希）總統簽署成為法律，其中修訂美國法典 (21 USC 830)中有關銷售含有麻黃鹼和密切相關的偽麻黃鹼的產品。這兩種物質都被用作生產甲基安非他命的前體，為阻止這類非法使用，聯邦法對銷售此類產品的商家提出以下要求：

  • 所有購買均須留下記錄，標明買方的姓名和地址，記錄保存兩年
  • 需要驗證所有購買者的身份證明
  • 對收集的個人資訊提供的保護和揭露方法
  • 向美國司法部長報告任何可疑付款或受管制產品失踪的情況
  • 受管制產品中的非液體劑型只能以單位劑量泡罩包裝出售
  • 受管制產品應在櫃檯後面或上鎖的櫃子中保存，以管制接觸
  • 每日向單一購買者銷售的受管制產品不得超過3.6克，（不論交易數量）
  • 每月向單一購買者銷售的受管制產品中的偽麻黃鹼含量不得超過9克

法案對採郵購購買方式有類似的規定，但每月銷售限量為7.5克。

含有麻黃鹼的純草藥或茶在美國仍可合法銷售。法律限制/禁止其作為膳食補充劑（片劑）或作為其他產品（如減肥藥）的成分/添加劑出售。

澳大利亞

麻黃鹼和所有包包含它的麻黃屬物種均被視為《藥物和毒物的統一調度標準》中附表4物質。附表4藥物被視為純處方藥物或處方動物藥物 - 只有經州或地區允許的人才能使用或供應的物質，並且應根據前述《調度標準準》由藥劑師按照處方箋提供。

南非

在南非，麻黃鹼於2008年5月27日移至《1965年藥品及相關物質法》附表6中，[60]使得純麻黃鹼片劑僅能作為處方藥。每片含麻黃鹼最多30毫克的片劑與其他藥物組合仍可作為非處方藥使用（附表1和2），用於治療鼻竇、感冒和流行性感冒。

德國

麻黃鹼於2001年之前可在德國的藥房中自由購買。之後由於購買均非作治療用途，因而受到管制。同樣的，購買麻黃也只能憑處方從事。自2006年4月起，所有含有麻黃鹼的產品，包括植物部分，都必須憑處方箋才能購買。[61]

來源

傳統上麻黃鹼是從植物麻黃和麻黃屬的其他成員中萃取。麻黃鹼和中藥原料在中國大量生產。截至2007年，中國各公司每年從3萬噸麻黃（約為中藥用量的十倍）中生產價值1,300萬美元的麻黃素作出口用途。[62]

有採用苯甲醛、肉桂酸和 1-苯基丙酮等進行化學合成麻黃鹼及偽麻黃鹼的報導。[63]

麻黃鹼的假設生物合成途徑 - 徑涉及左旋-苯丙氨酸和丙酮酸兩種化合物的轉化。[64][65]

也有研究人員探討以生物合成途經生產麻黃鹼的方式。[66][64][65]








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