THC (Δ9-THC)
Chemistry
- Formula
- C21H30O2
- Molar mass
- 314.5 g/mol
- IUPAC name
- (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
- InChIKey
- CYQFCXCEBYINGO-IAGOWNOFSA-N
Chemistry from PubChem CID 16078.
Also known as
- Dronabinol
- TETRAHYDROCANNABINOL
- Marinol
- delta9-Tetrahydrocannabinol
- delta9-THC
- delta-9-tetrahydrocannabinol
- Abbott 40566
- 1972-08-3
Stereoisomers
4 distinct stereoisomers are registered for this structure.
- Tetrahydrocannabinol this area CID 16078
- 6H-Dibenzo(b,d)pyran-1-ol, 6a-beta,7,8,10-a-beta-tetrahydro-3-pentyl-6,6,9-trimethyl-, (+-)-Z- CID 22462
- (6aS,10aS)-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo(b,d)pyran-1-ol CID 134740
- delta9-CIS-TETRAHYDROCANNABINOL, (-)- CID 12831993
- 6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo(c)chromen-1-ol mixture CID 2978
The THC in cannabis is one specific isomer, (−)-trans-Δ9-THC. Its mirror image is far less active and does not occur naturally. This is a different question from the Δ8 / Δ9 distinction, which is about where a double bond sits rather than about handedness.
Attribution
- Raphael Mechoulam — isolated it, 1964
Structure elucidated 1964, total synthesis 1965.
- Yechiel Gaoni — isolated it, 1964
Joint first author on the structure and synthesis papers.
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