Heptaminol

Heptaminol

IUPAC name (RS)-6-amino-2-methylheptan-2-ol
Identifiers
CAS number	372-66-7^Y
PubChem	3590
ChemSpider	3464^Y
MeSH	Heptaminol
ATC code	C01DX08
Jmol-3D images	Image 1
SMILES OC(C)(C)CCCC(N)C
InChI InChI=1S/C8H19NO/c1-7(9)5-4-6-8(2,3)10/h7,10H,4-6,9H2,1-3H3^Y Key: LREQLEBVOXIEOM-UHFFFAOYSA-N^Y
Properties
Molecular formula	C₈H₁₉NO
Molar mass	145.24 g mol⁻¹
Pharmacology
Routes of administration	Oral, intravenous, intramuscular
Excretion	Renal
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Heptaminol is an amino alcohol which is classified as a vasoconstrictor (C01DX08). It is sometimes used in the treatment of low blood pressure, particularly orthostatic hypotension.^[1]

It is classified as a doping substance, in 2008 the cyclist Dmitriy Fofonov was tested positive at the Tour de France^[2]. In 2010 June the swimmer Frédérick Bousquet was tested positive for the substance, allegedly for buying a medicine from the pharmacy^[3].

References [link]

^ (French) "Heptaminol Chlorhydrate". BIAM. March 3, 2000. https://www.biam2.org/www/Sub1530.html. Retrieved 2007-02-27.
^ "Tour rider Fofonov tests positive". BBC. 2008-07-28. https://news.bbc.co.uk/sport2/hi/other_sports/cycling/7527891.stm. Retrieved 2008-07-28.
^ "France swimmer Bousquet suspended in doping scandal". France24. 2010-10-24. https://www.france24.com/en/20101020-france-swimmer-bousquet-serving-doping-suspension-scandal-sport. Retrieved 2010-10-23.

v t e Stimulants (N06B)

Adamantanes	Adaphenoxate Adapromine Amantadine Bromantane Chlodantane Gludantane Memantine Midantane

Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Paraxanthine SCH-58261 Theobromine Theophylline

Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane

Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine

Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958

Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 TC-5619 Tebanicline UB-165 Varenicline WAY-317,538

Convulsants	Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone

Eugeroics	Adrafinil Armodafinil CRL-40941 Modafinil

Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone

Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Phenyl-2-(piperidin-1-yl)pentan-3-one 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2-Phenyl-3-methylaminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-Ethylamphetamine 4-FA 4-FMA 4-MA 4-MMA 4-MTA 6-FNE Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone Amidephrine Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine ß-Methylphenethylamine ß-Phenylmethamphetamine Benfluorex Benzedrone Benzphetamine BDB BOH BPAP Buphedrone Bupropion Butylone Cathine Cathinone Chlorphentermine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylamphetamine Ethylnorepinephrine Ethylone Etilefrine Famprofazone Fenbutrazate Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenmetramide Fenproporex Flephedrone Fludorex Furfenorex Gepefrine Hexapradol HMMA Hordenine Hydroxyamphetamine Ibopamine IMP Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine Manifaxine MBDB MDA MDBU MDEA MDMA MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylone MMDA MMDMA MMMA Morazone N-Benzyl-1-phenethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxilofrine PBA PCA PHA Pargyline Pentorex Pentylone Phenatine Phendimetrazine Phenmetrazine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Pseudophenmetrazine Radafaxine Ropinirole Salbutamol (Levosalbutamol) Sibutramine Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xamoterol Xylopropamine Zylofuramine

Piperazines	2C-B-BZP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP Vanoxerine

Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 1-(3,4-Dichlorophenyl)-1-(piperidin-2-yl)butane 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylphenidate Methylnaphthidate Methylphenidate (Dexmethylphenidate) N-Methyl-3ß-propyl-4ß-(4-chlorophenyl)piperidine Nocaine Phacetoperane Pipradrol SCH-5472

Pyrrolidines	2-Diphenylmethylpyrrolidine a-PPP a-PBP a-PVP Diphenylprolinol MDPPP MDPBP MDPV MPBP MPHP MPPP MOPPP Naphyrone PEP Prolintane Pyrovalerone

Tropanes	3-CPMT 3'-Chloro-3a-(diphenylmethoxy)tropane 3-Pseudotropyl-4-fluorobenzoate 4'-Fluorococaine AHN-1055 Altropane (IACFT) Brasofensine CFT (WIN 35,428) ß-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-ß-CPPIT FP-ß-CPPIT Ioflupane (¹²³I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-105 RTI-112 RTI-113 RTI-117 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-154 RTI-171 RTI-177 RTI-183 RTI-193 RTI-194 RTI-199 RTI-202 RTI-204 RTI-229 RTI-241 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (ß-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33 WF-60

Others	1-(Thiophen-2-yl)-2-aminopropane 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 2-Aminotetralin 2-MDP 2-Phenylcyclohexylamine 2-Phenyl-3,6-dimethylmorpholine 3-Benzhydrylmorpholine 3,3-Diphenylcyclobutanamine 5-(2-Aminopropyl)indole 5-Iodo-2-aminoindane AL-1095 Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Camfetamine Carphedon Ciclazindol Cilobamine Clofenciclan Cropropamide Crotetamide Cypenamine D-161 Diclofensine Dimethocaine Efaroxan Etamivan EXP-561 Fencamfamine Fenpentadiol Feprosidnine G-130 Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 JZ-IV-10 Lazabemide Leptacline Levopropylhexedrine Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Mesocarb Methastyridone Methiopropamine N-Methyl-3-phenylnorbornan-2-amine Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline Phthalimidopropiophenone PNU-99,194 Propylhexedrine PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Trazium UH-232 Yohimbine

See also Sympathomimetic amines

v t e Amines, alcohols: amino alcohols

Ethanolamine Heptaminol Isoetarine Norepinephrine Propanolamine Sphingosine

Vasodilators used in cardiac diseases (C01D)

Nitrates/nitrovasodilators

Glyceryl trinitrate # • Isosorbide dinitrate # • Isosorbide mononitrate • Linsidomine • Molsidomine • Pentaerythritol tetranitrate • Propatylnitrate • Tenitramine • Trolnitrate

Quinolone vasodilators

Flosequinan^‡

Others

Itramin tosilate • Prenylamine • Oxyfedrine • Benziodarone • Carbocromen • Hexobendine • Etafenone • Heptaminol • Imolamine • Dilazep • Trapidil • Molsidomine • Efloxate • Cinepazet • Cloridarol • Nicorandil • Nesiritide • Gapicomine • Pimobendan

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: HRT

anat/phys/devp

noco/cong/tumr, sysi/epon, injr

proc, drug (C1A/1B/1C/1D), blte

Adrenergics

Receptor ligands

α₁	Agonists: 5-FNE 6-FNE Amidephrine Anisodamine Anisodine Cirazoline Dipivefrine Dopamine Ephedrine Epinephrine Etilefrine Ethylnorepinephrine Indanidine Levonordefrin Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetrahydrozoline Antagonists: Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Arotinolol Atiprosin Benoxathian Buflomedil Bunazosin Carvedilol CI-926 Corynanthine Dapiprazole DL-017 Domesticine Doxazosin Eugenodilol Fenspiride GYKI-12,743 GYKI-16,084 Indoramin Ketanserin L-765,314 Labetalol Mephendioxan Metazosin Monatepil Moxisylyte Naftopidil Nantenine Neldazosin Nicergoline Niguldipine Pelanserin Phendioxan Phenoxybenzamine Phentolamine Piperoxan Prazosin Quinazosin Ritanserin RS-97,078 SGB-1,534 Silodosin SL-89.0591 Spiperone Talipexole Tamsulosin Terazosin Tibalosin Tiodazosin Tipentosin Tolazoline Trimazosin Upidosin Urapidil Zolertine * Note that many TCAs, TeCAs, antipsychotics, ergolines, and some piperazines like buspirone and trazodone all antagonize α₁-adrenergic receptors as well, which contributes to their side effects such as orthostatic hypotension.

α₂	Agonists: (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Ephedrine Ergotamine Epinephrine Esproquin Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz Levonordefrin Lofexidine Medetomidine Methyldopa Mivazerol Naphazoline Norepinephrine Phenylpropanolamine Piperoxan Pseudoephedrine Rilmenidine Romifidine Talipexole Tetrahydrozoline Tizanidine Tolonidine Urapidil Xylazine Xylometazoline Antagonists: 1-PP Adimolol Aptazapine Atipamezole BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan GYKI-12,743 GYKI-16,084 Idazoxan Mianserin Mirtazapine MK-912 NAN-190 Olanzapine Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine SB-269,970 Setiptiline Spiroxatrine Sunepitron Tolazoline Yohimbine * Note that many atypical antipsychotics and azapirones like buspirone (via metabolite 1-PP) antagonize α₂-adrenergic receptors as well.

β	Agonists: 2-FNE 5-FNE Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Cimaterol Clenbuterol Denopamine Deterenol Dipivefrine Dobutamine Dopamine Dopexamine Ephedrine Epinephrine Etafedrine Etilefrine Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine Labetalol Levonordefrin Levosalbutamol Mabuterol Methoxyphenamine Methyldopa N-Isopropyloctopamine Norepinephrine Orciprenaline Oxyfedrine Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Xamoterol Zilpaterol Zinterol Antagonists: Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bormetolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Buftiralol Bufuralol Bunitrolol Bunolol Bupranolol Burocrolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Dropranolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esmolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levocicloprolol Levomoprolol Medroxalol Mepindolol Metalol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nafetolol Nebivolol Neraminol Nifenalol Nipradilol Oberadilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Parodilol Penbutolol Penirolol PhQA-33 Pindolol Pirepolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol TA-2005 Talinolol Tazolol Teoprolol Tertatolol Terthianolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Tribendilol Trigevolol Xibenolol Xipranolol

Reuptake inhibitors

NET	Selective norepinephrine reuptake inhibitors: Amedalin Atomoxetine (Tomoxetine) Ciclazindol Daledalin Edivoxetine Esreboxetine Lortalamine Mazindol Nisoxetine Reboxetine Talopram Talsupram Tandamine Viloxazine; Norepinephrine-dopamine reuptake inhibitors: Amineptine Bupropion (Amfebutamone) Fencamine Fencamfamine Lefetamine Levophacetoperane LR-5182 Manifaxine Methylphenidate Nomifensine O-2172 Radafaxine; Serotonin-norepinephrine reuptake inhibitors: Bicifadine Desvenlafaxine Duloxetine Eclanamine Levomilnacipran Milnacipran Sibutramine Venlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors: Brasofensine Diclofensine DOV-102,677 DOV-21,947 DOV-216,303 JNJ-7925476 JZ-IV-10 Methylnaphthidate Naphyrone NS-2359 PRC200-SS SEP-225,289 SEP-227,162 Tesofensine; Tricyclic antidepressants: Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin Doxepin Imipramine Lofepramine melitracen Nortriptyline Protriptyline Trimipramine; Tetracyclic antidepressants: Amoxapine Maprotiline Mianserin Oxaprotiline Setiptiline; Others: Cocaine CP-39,332 EXP-561 Fezolamine Ginkgo biloba Indeloxazine Nefazodone Nefopam Pridefrine Tapentadol Tedatioxetine Teniloxazine Tofenacin Tramadol Ziprasidone

VMAT	Ibogaine Reserpine Tetrabenazine

Releasing agents

Morpholines: Fenbutrazate
Fenmetramide
Morazone
Phendimetrazine
Phenmetrazine
Pseudophenmetrazine; Oxazolines: 4-MAR
Aminorex
Clominorex
Cyclazodone
Fenozolone
Fluminorex
Pemoline
Thozalinone; Phenethylamines (also amphetamines, cathinones, etc): 2-OH-PEA
4-CAB
4-FA
4-FMA
4-MA
4-MMA
Alfetamine
Amfecloral
Amfepentorex
Amfepramone
Amphetamine (Dextroamphetamine
Levoamphetamine)
Amphetaminil
β-Me-PEA
BDB
Benzphetamine
BOH
Buphedrone
Butylone
Cathine
Cathinone
Clobenzorex
Clortermine
Dimethylamphetamine
Dimethylcathinone
DMA
DMMA
EBDB
Ephedrine
Ethcathinone
Ethylamphetamine
Ethylone
Famprofazone
Fenethylline
Fenproporex
Flephedrone
Fludorex
Furfenorex
Hordenine
Hydroxyamphetamine
IAP
IMP
Iofetamine
Lisdexamfetamine
Lophophine
MBDB
MDA
MDEA
MDMA
MDMPEA
MDOH
MDPEA
Mefenorex
Mephedrone
Mephentermine
Methamphetamine (Dextromethamphetamine
Levomethamphetamine)
Methcathinone
Methedrone
Methylone
Naphthylisopropylamine
Ortetamine
pBA
pCA
Pentorex
Phenethylamine
Pholedrine
Phenpromethamine
Phentermine
Phenylpropanolamine
pIA
Prenylamine
Propylamphetamine
Pseudoephedrine
Selegiline (also D-Deprenyl)
Tiflorex
Tyramine
Xylopropamine
Zylofuramine; Piperazines: 2C-B-BZP
BZP
MBZP
mCPP
MDBZP
MeOPP
pFPP; Others: 2-ADN
2-AI
2-AT
2-BP
4-BP
5-IAI
Clofenciclan
Cyclopentamine
Cypenamine
Cyprodenate
Feprosidnine
Gilutensin
Heptaminol
Hexacyclonate
Indanorex
Isometheptene
Methylhexanamine
Octodrine
Phthalimidopropiophenone
Propylhexedrine (Levopropylhexedrine)
Tuaminoheptane

Enzyme inhibitors

Anabolism

PAH	3,4-Dihydroxystyrene

TH	3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

AAAD	Benserazide Carbidopa DFMD Genistein Methyldopa

DBH	Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone

PNMT	CGS-19281A SKF-64139 SKF-7698

Catabolism

MAO	Nonselective: Benmoxin Caroxazone Echinopsidine Furazolidone Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivalylbenzhydrazine Procarbazine Safrazine Tranylcypromine; MAO-A selective: Amiflamine Bazinaprine Befloxatone Befol Brofaromine Cimoxatone Clorgiline Esuprone Harmala alkaloids (Harmine, Harmaline Tetrahydroharmine Harman Norharman, etc) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone Tyrima; MAO-B selective: Ladostigil Lazabemide Milacemide Mofegiline Pargyline Rasagiline Safinamide Selegiline (also [[D-Deprenyl]]) * Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.

COMT	Entacapone Nitecapone Tolcapone

Others

Precursors	L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine L-DOPS (Droxidopa)

Cofactors	Ferrous Iron (Fe²⁺) S-Adenosyl-L-Methionine Vitamin B₃ (Niacin Nicotinamide → NADPH) Vitamin B₆ (Pyridoxine Pyridoxamine Pyridoxal → Pyridoxal Phosphate) Vitamin B₉ (Folic acid → Tetrahydrofolic acid) Vitamin C (Ascorbic acid) Zinc (Zn²⁺)

Others	Activity enhancers: BPAP PPAP; Release blockers: Bethanidine Bretylium Guanadrel Guanazodine Guanclofine Guanethidine Guanoxan; Toxins: 6-OHDA

List of adrenergic drugs

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References [link]

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