AM-905

AM-905
Identifiers
	IUPAC name (6aR,9R,10aR)-3-[(E)-hept-1-enyl]-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol;
CAS Number	181139-62-8 ;
PubChem CID	9998522;
ChemSpider	8174103 ;
UNII	TJ6JD73J07;
ChEMBL	ChEMBL127848 ;
Chemical and physical data
Formula	C23H34O3
Molar mass	358.522 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCC/C=C/c(cc1O)cc(OC(C)(C)C2CC3)c1C2CC3CO;
	InChI InChI=1S/C23H34O3/c1-4-5-6-7-8-9-16-13-20(25)22-18-12-17(15-24)10-11-19(18)23(2,3)26-21(22)14-16/h8-9,13-14,17-19,24-25H,4-7,10-12,15H2,1-3H3/b9-8+/t17-,18-,19-/m1/s1 ; Key:NJIKRWBGUIYKJM-OKMMTOMJSA-N ;
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Short description: Chemical compound

AM-905 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is conformationally restricted by virtue of the double bond on its side chain, leading an increased affinity for and selectivity between CB₁ and CB₂ receptors.^[1] It is a potent and reasonably selective agonist for the CB₁ cannabinoid receptor, with a K_i of 1.2 nM at CB₁ and 5.3 nM at CB₂.^[2]

References

↑ "Unsaturated side chain beta-11-hydroxyhexahydrocannabinol analogs". Journal of Medicinal Chemistry 39 (19): 3790–6. September 1996. doi:10.1021/jm950934b. PMID 8809166.
↑ "Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols". Journal of Medicinal Chemistry 41 (7): 1195–200. March 1998. doi:10.1021/jm970277i. PMID 9544219.

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Original source: https://en.wikipedia.org/wiki/AM-905. Read more

[Busch-PetersenHill1996-1] "Unsaturated side chain beta-11-hydroxyhexahydrocannabinol analogs". Journal of Medicinal Chemistry 39 (19): 3790–6. September 1996. doi:10.1021/jm950934b. PMID 8809166.

[2] "Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols". Journal of Medicinal Chemistry 41 (7): 1195–200. March 1998. doi:10.1021/jm970277i. PMID 9544219.

[1]

[2]

AM-905

Topic: Chemistry

See also

References

Identifiers

IUPAC name (6aR,9R,10aR)-3-[(E)-hept-1-enyl]-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
CAS Number	181139-62-8^Y
PubChem CID	9998522
ChemSpider	8174103^Y
UNII	TJ6JD73J07
ChEMBL	ChEMBL127848^Y
Chemical and physical data
Formula	C₂₃H₃₄O₃
Molar mass	358.522 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCC/C=C/c(cc1O)cc(OC(C)(C)C2CC3)c1C2CC3CO
InChI InChI=1S/C23H34O3/c1-4-5-6-7-8-9-16-13-20(25)22-18-12-17(15-24)10-11-19(18)23(2,3)26-21(22)14-16/h8-9,13-14,17-19,24-25H,4-7,10-12,15H2,1-3H3/b9-8+/t17-,18-,19-/m1/s1^Y Key:NJIKRWBGUIYKJM-OKMMTOMJSA-N^Y
(verify)