Dimethylheptylpyran

Dimethylheptylpyran
Clinical data
Other names	3-(1,2-dimethylheptyl)-Δ6a(10a)-THC, 1,2-dimethylheptyl-Δ3-THC, A-40824, EA-2233
Drug class	Cannabinoid
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); DE: Anlage I (Authorized scientific use only); UK: Class B; US: Schedule I; UN: Psychotropic Schedule I;
Pharmacokinetic data
Elimination half-life	20–39 hours
Identifiers
	IUPAC name 6,6,9-Trimethyl-3-(3-methyl-2-octanyl)-7,8,9,10-tetrahydro-6H-benzo[c]chromen-1-ol;
CAS Number	32904-22-6 ;
PubChem CID	36276;
ChemSpider	33359 ;
UNII	944O1KA97G;
KEGG	C22734 ;
ChEMBL	ChEMBL3244434 ;
CompTox Dashboard (EPA)	DTXSID60954555 ;
Chemical and physical data
Formula	C25H38O2
Molar mass	370.577 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC(C)C(C)c1cc(c2c(c1)OC(C3=C2CC(CC3)C)(C)C)O;
	InChI InChI=1S/C25H38O2/c1-7-8-9-10-17(3)18(4)19-14-22(26)24-20-13-16(2)11-12-21(20)25(5,6)27-23(24)15-19/h14-18,26H,7-13H2,1-6H3 ; Key:QBEFIFWEOSUTKV-UHFFFAOYSA-N ;
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Dimethylheptylpyran (DMHP) is a synthetic cannabinoid and analogue of tetrahydrocannabinol (THC). It was invented in 1949 during attempts to elucidate the structure of Δ⁹-THC, one of the active components of cannabis.^[2] DMHP is a pale yellow, viscous oil which is insoluble in water but dissolves in alcohol or non-polar solvents.

DMHP is similar in structure to THC, differing only in the position of one double bond, and the replacement of the 3-pentyl chain with a 3-(1,2-dimethylheptyl) chain.^[3]

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ Adams R, Harfenist M, Loewe S (1949). "New Analogs of Tetrahydrocannabinol. XIX". Journal of the American Chemical Society. 71 (5): 1624–1628. doi:10.1021/ja01173a023.
^ Razdan RK (1980). "The Total Synthesis of Cannabinoids". Total Synthesis of Natural Products. Vol. 4. Wiley-Interscience. pp. 185–262. doi:10.1002/9780470129678.ch2. ISBN 978-0-471-05460-3.

[1] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[2] Adams R, Harfenist M, Loewe S (1949). "New Analogs of Tetrahydrocannabinol. XIX". Journal of the American Chemical Society. 71 (5): 1624–1628. doi:10.1021/ja01173a023.

[3] Razdan RK (1980). "The Total Synthesis of Cannabinoids". Total Synthesis of Natural Products. Vol. 4. Wiley-Interscience. pp. 185–262. doi:10.1002/9780470129678.ch2. ISBN 978-0-471-05460-3.

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