Anandamid

Anandamid
	(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
Drugi nazivi	N-arahidonoil tanolamin; arahidonoil etanolamid
Identifikacija
CAS registarski broj	94421-68-8
PubChem	5281969
ChemSpider	4445241
MeSH	Anandamide
ChEMBL	CHEMBL15848
IUPHAR ligand	737
Jmol-3D slike	Slika 1; Slika 2
SMILES
	O=C(NCCO)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO
InChI
	InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15- ; Kod: LGEQQWMQCRIYKG-DOFZRALJSA-N InChI=1/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-; Kod: LGEQQWMQCRIYKG-DOFZRALJBA
Svojstva
Molekulska formula	C22H37NO2
Molarna masa	347.53 g/mol
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Anandamid, N-arahidonoil tanolamin ili AEA, je endogeni kanabinoidni neurotransmiter. Njega su izolovali i opisali češki analitički hemičar Lumír Ondrej Hanuš i američki molekularni farmakolog Vilijam Antoni Devan 1992. Ime je potiče od Sanskritske reči ananda, što znači blaženstvo, oduševljenje, i amid.^[5]^[6]

On se može sintetisati iz N-arahidonoil fosfatidiletanolamina na više načina.^[7] Njega prvenstveno degradira enzim FAAH, koji konvertuje anandamid u etanolamin i arahidonsku kiselinu. Usled toga, FAAH inhibitori dovode do povišenih nivoa anandamida i imaju terapeutsku primenu.^[8]^[9]

Fiziološke funkcije

Efekti anandamida mogu da budu bilo centralni, u mozgu, ili periferni, u drugim delovima tela. Ti distinktni efekti su posredovani prvenstveno CB1 kanabinoidnim receptorima u centralnom nervnom sistemu, i CB2 kanabinoidnim receptorima na periferiji.^[10] Na periferiji anandamid uglavnom učestvuje u funkcijama imunskog sistema. Kanabinoidni receptori su originalno otkriveni na osnovu njihove senzitivnosti na Δ⁹-tetrahidrokanabinol (Δ⁹-THC), koji je psihoaktivni kanabinoid nađen u kanabisu. Otkriće anandamida potiče iz CB1 i CB2 istraživanja, kaja su delom bila zasnovana na stanovištu da mora da postoji prirodna (endogena) hemikalija koja se vezuje za te receptore.

Povezano

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Devane WA, Hanus L, Breuer A, Pertwee RG, Stevenson LA, Griffin G, Gibson D, Mandelbaum A, Etinger A, Mechoulam R (December 1992). „Isolation and structure of a brain constituent that binds to the cannabinoid receptor”. Science 258 (5090): 1946–9. DOI:10.1126/science.1470919. PMID 1470919.
↑ Mechoulam R, Fride E (1995). „The unpaved road to the endogenous brain cannabinoid ligands, the anandamides”. u: Pertwee RG. Cannabinoid receptors. Boston: Academic Press. str. 233–258. ISBN 0-12-551460-3.
↑ Wang J, Ueda N (September 2009). „Biology of endocannabinoid synthesis system”. Prostaglandins & Other Lipid Mediators 89 (3-4): 112–9. DOI:10.1016/j.prostaglandins.2008.12.002. PMID 19126434.
↑ Gaetani S, Dipasquale P, Romano A, Righetti L, Cassano T, Piomelli D, Cuomo V (2009). „The endocannabinoid system as a target for novel anxiolytic and antidepressant drugs”. International Review of Neurobiology 85: 57–72. DOI:10.1016/S0074-7742(09)85005-8. PMID 19607961.
↑ Hwang J, Adamson C, Butler D, Janero DR, Makriyannis A, Bahr BA (April 2010). „Enhancement of endocannabinoid signaling by fatty acid amide hydrolase inhibition: a neuroprotective therapeutic modality”. Life Sciences 86 (15-16): 615–23. DOI:10.1016/j.lfs.2009.06.003. PMID 19527737.
↑ Pacher P, Batkai S, Kunos G (2006). „The endocannabinoid system as an emerging target of pharmacotherapy.”. Pharmacol Rev.. DOI:10.1124/pr.58.3.2. PMC 2241751. PMID 16968947.

Literatura

Spoljašnje veze

Portal Hemija

Could anandamide be the missing link to "runner's high"? Arhivirano 2012-11-08 na Wayback Machine-u Accessed 2008-10-18

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[pmid1470919-5] Devane WA, Hanus L, Breuer A, Pertwee RG, Stevenson LA, Griffin G, Gibson D, Mandelbaum A, Etinger A, Mechoulam R (December 1992). „Isolation and structure of a brain constituent that binds to the cannabinoid receptor”. Science 258 (5090): 1946–9. DOI:10.1126/science.1470919. PMID 1470919.

[isbn0-12-551460-3-6] Mechoulam R, Fride E (1995). „The unpaved road to the endogenous brain cannabinoid ligands, the anandamides”. u: Pertwee RG. Cannabinoid receptors. Boston: Academic Press. str. 233–258. ISBN 0-12-551460-3.

[pmid19126434-7] Wang J, Ueda N (September 2009). „Biology of endocannabinoid synthesis system”. Prostaglandins & Other Lipid Mediators 89 (3-4): 112–9. DOI:10.1016/j.prostaglandins.2008.12.002. PMID 19126434.

[pmid19607961-8] Gaetani S, Dipasquale P, Romano A, Righetti L, Cassano T, Piomelli D, Cuomo V (2009). „The endocannabinoid system as a target for novel anxiolytic and antidepressant drugs”. International Review of Neurobiology 85: 57–72. DOI:10.1016/S0074-7742(09)85005-8. PMID 19607961.

[pmid19527737-9] Hwang J, Adamson C, Butler D, Janero DR, Makriyannis A, Bahr BA (April 2010). „Enhancement of endocannabinoid signaling by fatty acid amide hydrolase inhibition: a neuroprotective therapeutic modality”. Life Sciences 86 (15-16): 615–23. DOI:10.1016/j.lfs.2009.06.003. PMID 19527737.

[pmid16968947-10] Pacher P, Batkai S, Kunos G (2006). „The endocannabinoid system as an emerging target of pharmacotherapy.”. Pharmacol Rev.. DOI:10.1124/pr.58.3.2. PMC 2241751. PMID 16968947.

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