(1-Pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone

(1-Pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone

Systematic (IUPAC) name
(1-pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone
Clinical data
Pregnancy cat.	?
Legal status	uncontrolled
Identifiers
ATC code	?
PubChem	CID 44626619
Chemical data
Formula	C21H29NO
Mol. mass	311.461 g/mol
SMILES	eMolecules & PubChem

(1-Pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone is a drug invented by Abbott Laboratories,^[1] that acts as a selective full agonist of the peripheral cannabinoid receptor CB₂, but with much lower affinity for the psychoactive CB₁ receptor. It has high affinity for the CB₂ receptor with a K_i of 1.8nM but 83x lower affinity for the CB₁ receptor with a K_i of 150nM.^[2] Chemically it is closely related to other 2,2,3,3-tetramethylcyclopropyl synthetic cannabinoids like A-796,260 and A-834,735 but with a different substitution on the 1-position of indole core, its 1-pentyl group replaced with alkylheterocycles like 1-(2-morpholinoethyl) and 1-(tetrahydropyran-4-ylmethyl).

See also

• AB-001
• JWH-018
• N-(S)-Fenchyl-1-(2-morpholinoethyl)-7-methoxyindole-3-carboxamide

References

1. ^ WO application 2006069196, Pace JM, Tietje K, Dart MJ, Meyer MD, "3-Cycloalkylcarbonyl indoles as cannabinoid receptor ligands", published 2006-06-29, assigned to Abbott Laboratories 
2. ^ Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, El-Kouhen OF, Yao BB, Hsieh GC, Pai M, Zhu CZ, Chandran P, Meyer MD (January 2010). "Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity". J. Med. Chem. 53 (1): 295–315. doi:10.1021/jm901214q. PMID 19921781. 

Further reading

• Poso A, Huffman JW (January 2008). "Targeting the cannabinoid CB2 receptor: modelling and structural determinants of CB2 selective ligands". Br. J. Pharmacol. 153 (2): 335–46. doi:10.1038/sj.bjp.0707567. PMC 2219524. PMID 17982473. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2219524. 
• Chin CL, Tovcimak AE, Hradil VP, Seifert TR, Hollingsworth PR, Chandran P, Zhu CZ, Gauvin D, Pai M, Wetter J, Hsieh GC, Honore P, Frost JM, Dart MJ, Meyer MD, Yao BB, Cox BF, Fox GB (January 2008). "Differential effects of cannabinoid receptor agonists on regional brain activity using pharmacological MRI". Br. J. Pharmacol. 153 (2): 367–79. doi:10.1038/sj.bjp.0707506. PMC 2219521. PMID 17965748. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2219521. 
• Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, El-Kouhen OF, Miller LN, Li L, Yao BB, Hsieh GC, Pai M, Zhu CZ, Chandran P, Meyer MD (March 2008). "Indol-3-yl-tetramethylcyclopropyl ketones: effects of indole ring substitution on CB2 cannabinoid receptor activity". J. Med. Chem. 51 (6): 1904–12. doi:10.1021/jm7011613. PMID 18311894. 

This cannabinoid related article is a stub. You can help Wikipedia by expanding it.v · Categories: Cannabinoids Cyclopropanes Cannabinoid stubs Wikimedia Foundation. 2010. Игры ⚽ Нужно сделать НИР? (Mesitylene)molybdenum tricarbonyl (100003) 1983 RN3 Look at other dictionaries: N-(S)-Fenchyl-1-(2-morpholinoethyl)-7-methoxyindole-3-carboxamide — Systematic (IUPAC) name 7 methoxy 1 (2 morpholinoethyl) N ((1S,2S,4R) 1,3,3 trimethylbicyclo[2.2.1]heptan 2 yl) 1H indole 3 carboxamide C …   Wikipedia RCS-4 — Systematic (IUPAC) name 2 (4 methoxyphenyl) 1 (1 pentyl indol 3 yl)methanone Clinical data Pregnancy cat …   Wikipedia Org 28312 — Systematic (IUPAC) name [1 (cyclohexylmethyl) 7 methoxyindol 3 yl] ((3S,5R) 3,4,5 trimethylpiperazin 1 yl)methanone Clinical data Pregnancy cat …   Wikipedia Org 28611 — Systematic (IUPAC) name [1 (cyclohexylmethyl) 7 methoxyindol 3 yl] [(3S) 3,4 dimethylpiperazin 1 yl]methanone Clinical data Pregnancy cat …   Wikipedia Tetrahydrocannabinol — THC redirects here. For other uses, see THC (disambiguation). Tetrahydrocannabinol (THC) …   Wikipedia Paracetamol — Acetaminophen Systematic (IUPAC) name …   Wikipedia Anandamide — IUPAC name (5Z,8Z,11Z,14Z) N (2 hydroxyethyl)icosa 5,8,11,14 tetraenamide …   Wikipedia Effects of cannabis — Short term effects of cannabis Classification and external resources ICD 10 F12.0 The effects of cannabis are caused by cannabinoids, most notably tetrahydrocannabinol (THC). Cannabis has both psychological and physiological effects on the human… …   Wikipedia Cannabis (drug) — Marijuana redirects here. For other uses, see Marijuana (disambiguation). For the plant genus, see Cannabis. Cannabis …   Wikipedia Nabilone — Systematic (IUPAC) name (6aR,10aR) rel 1 hydroxy 6,6 dimethyl 3 (2 methyloctan 2 yl) Clinical data AHFS/ …   Wikipedia 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”