Tetrahydrocannabutol information

Δ⁹-Tetrahydrocannabinol-C4
Clinical data
ATC code	none;
Identifiers
	IUPAC name (−)-(6aR,10aR)-6,6,9-trimethyl-3-butyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol;
CAS Number	60008-00-6 ;
PubChem CID	6453891;
ChemSpider	4956237 ;
UNII	LIC9QAS59U;
ChEMBL	ChEMBL4437290;
CompTox Dashboard (EPA)	DTXSID10208712 ;
Chemical and physical data
Formula	C20H28O2
Molar mass	300.442 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)O;
	InChI InChI=1S/C20H28O2/c1-5-6-7-14-11-17(21)19-15-10-13(2)8-9-16(15)20(3,4)22-18(19)12-14/h10-12,15-16,21H,5-9H2,1-4H3/t15-,16-/m1/s1 ; Key:QHCQSGYWGBDSIY-HZPDHXFCSA-N ;
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Δ⁹-Tetrahydrocannabutol (tetrahydrocannabinol-C4, THC-C4, Δ⁹-THCB, (C4)-Δ⁹-THC, butyl-THC) is a phytocannabinoid found in cannabis that is a homologue of tetrahydrocannabinol (THC), the main active component of Cannabis.^[1] Structurally, they are only different by the pentyl side chain being replaced by a butyl side chain. THCB was studied by Roger Adams as early as 1942 ^[2]

^ Linciano P, Citti C, Luongo L, Belardo C, Maione S, Vandelli MA, et al. (January 2020). "Isolation of a High-Affinity Cannabinoid for the Human CB1 Receptor from a Medicinal Cannabis sativa Variety: Δ⁹-Tetrahydrocannabutol, the Butyl Homologue of Δ⁹-Tetrahydrocannabinol". Journal of Natural Products. 83 (1): 88–98. doi:10.1021/acs.jnatprod.9b00876. PMID 31891265. S2CID 209519659.
^ Adams R, Loewe S, Smith CM, McPhee WD (1942). "Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII¹". Journal of the American Chemical Society. 64 (3): 694–697. doi:10.1021/ja01255a061.

[:0-1] Linciano P, Citti C, Luongo L, Belardo C, Maione S, Vandelli MA, et al. (January 2020). "Isolation of a High-Affinity Cannabinoid for the Human CB1 Receptor from a Medicinal Cannabis sativa Variety: Δ⁹-Tetrahydrocannabutol, the Butyl Homologue of Δ⁹-Tetrahydrocannabinol". Journal of Natural Products. 83 (1): 88–98. doi:10.1021/acs.jnatprod.9b00876. PMID 31891265. S2CID 209519659.

[2] Adams R, Loewe S, Smith CM, McPhee WD (1942). "Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII¹". Journal of the American Chemical Society. 64 (3): 694–697. doi:10.1021/ja01255a061.

Tetrahydrocannabutol information

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Clinical data


ATC code	none
Identifiers
IUPAC name (−)-(6aR,10aR)-6,6,9-trimethyl-3-butyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
CAS Number	60008-00-6^Y
PubChem CID	6453891
ChemSpider	4956237^Y
UNII	LIC9QAS59U
ChEMBL	ChEMBL4437290
CompTox Dashboard (EPA)	DTXSID10208712
Chemical and physical data
Formula	C₂₀H₂₈O₂
Molar mass	300.442 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)O
InChI InChI=1S/C20H28O2/c1-5-6-7-14-11-17(21)19-15-10-13(2)8-9-16(15)20(3,4)22-18(19)12-14/h10-12,15-16,21H,5-9H2,1-4H3/t15-,16-/m1/s1^N Key:QHCQSGYWGBDSIY-HZPDHXFCSA-N^N
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