Menabitan

Menabitan
Clinical data
ATC code	None;
Legal status
Legal status	US: Analogue to a Schedule I/II drug (Schedule I);
Identifiers
	IUPAC name [5,5-dimethyl-8-(3-methyloctan-2-yl)-2-prop-2-ynyl-3,4-dihydro-1H-chromeno[4,3-c]pyridin-10-yl] 2-methyl-4-(2-methylpiperidin-1-yl)butanoate;
CAS Number	83784-21-8 ; 58019-50-4 (HCl);
PubChem CID	189877;
ChemSpider	164903;
UNII	967H1G7V3P;
CompTox Dashboard (EPA)	DTXSID701003840 ;
Chemical and physical data
Formula	C37H56N2O3
Molar mass	576.866 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC(C)C(C)C1=CC2=C(C3=C(CCN(C3)CC#C)C(O2)(C)C)C(=C1)OC(=O)C(C)CCN4CCCCC4C;
	InChI InChI=1S/C37H56N2O3/c1-9-11-12-15-26(3)29(6)30-23-33(41-36(40)27(4)17-22-39-20-14-13-16-28(39)5)35-31-25-38(19-10-2)21-18-32(31)37(7,8)42-34(35)24-30/h2,23-24,26-29H,9,11-22,25H2,1,3-8H3; Key:ZWLPJYVIMWAEDC-UHFFFAOYSA-N;

Menabitan (INN; SP-204), or menabitan hydrochloride (USAN), is a synthetic drug which acts as a potent cannabinoid receptor agonist.^[1]^[2] It is closely related to natural cannabinoids of the tetrahydrocannabinol (THC) group, differing mainly by its longer and branched side chain, and the replacement of the 9-position carbon with a nitrogen. It's a structural analog of Nabitan and Dimethylheptylpyran.^[1] It was studied as an analgesic in the 1970s and was found to possess antinociceptive effects in both humans and animals but was never marketed.^[1]^[3]^[4]

Due to its structural similarity to the Schedule I/III drug THC it can be treated as a Schedule I drug within the United States legal system under the Federal Analogue Act.

References

^ ^a ^b ^c Green K, Kim K (February 1977). "Acute dose response of intraocular pressure to topical and oral cannabinoids". Proceedings of the Society for Experimental Biology and Medicine. 154 (2): 228–31. doi:10.3181/00379727-154-39643. PMID 402656. S2CID 32785623.
^ Triggle DJ (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. p. 1271. ISBN 978-0-412-46630-4.
^ Reggio PH (1987). "Molecular determinants for cannabinoid activity: refinement of a molecular reactivity template". NIDA Research Monograph. 79: 82–95. PMID 2830539.
^ Gabriel G. Nahas (5 April 1999). Marihuana and Medicine. Humana Press. p. 46. ISBN 978-0-89603-593-5. Retrieved 9 May 2012.

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[pmid402656-1] Green K, Kim K (February 1977). "Acute dose response of intraocular pressure to topical and oral cannabinoids". Proceedings of the Society for Experimental Biology and Medicine. 154 (2): 228–31. doi:10.3181/00379727-154-39643. PMID 402656. S2CID 32785623.

[isbn978-0-412-46630-4-2] Triggle DJ (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. p. 1271. ISBN 978-0-412-46630-4.

[pmid2830539-3] Reggio PH (1987). "Molecular determinants for cannabinoid activity: refinement of a molecular reactivity template". NIDA Research Monograph. 79: 82–95. PMID 2830539.

[Nahas1999-4] Gabriel G. Nahas (5 April 1999). Marihuana and Medicine. Humana Press. p. 46. ISBN 978-0-89603-593-5. Retrieved 9 May 2012.

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[2]

[3]

[4]

Clinical data

ATC code	None
Legal status
Legal status	US: Analogue to a Schedule I/II drug (Schedule I)
Identifiers
IUPAC name [5,5-dimethyl-8-(3-methyloctan-2-yl)-2-prop-2-ynyl-3,4-dihydro-1H-chromeno[4,3-c]pyridin-10-yl] 2-methyl-4-(2-methylpiperidin-1-yl)butanoate
CAS Number	83784-21-8^Y 58019-50-4 (HCl)
PubChem CID	189877
ChemSpider	164903
UNII	967H1G7V3P
CompTox Dashboard (EPA)	DTXSID701003840
Chemical and physical data
Formula	C₃₇H₅₆N₂O₃
Molar mass	576.866 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCC(C)C(C)C1=CC2=C(C3=C(CCN(C3)CC#C)C(O2)(C)C)C(=C1)OC(=O)C(C)CCN4CCCCC4C
InChI InChI=1S/C37H56N2O3/c1-9-11-12-15-26(3)29(6)30-23-33(41-36(40)27(4)17-22-39-20-14-13-16-28(39)5)35-31-25-38(19-10-2)21-18-32(31)37(7,8)42-34(35)24-30/h2,23-24,26-29H,9,11-22,25H2,1,3-8H3 Key:ZWLPJYVIMWAEDC-UHFFFAOYSA-N

Menabitan

See also

References