Stereochemical Requirements for Cannabinoid Activity

R. Mechoulam; N. Lander; T. H. Varkony; I. Kimmel; O. Becker; Z. Ben-Zvi; H. Edery; G. Porath

doi:10.1021/jm00184a002

Stereochemical Requirements for Cannabinoid Activity

R. Mechoulam, N. Lander, T. H. Varkony, I. Kimmel, O. Becker, Z. Ben-Zvi, H. Edery, G. Porath

Research output: Contribution to journal › Article › peer-review

49 Scopus citations

Abstract

Several pairs of cannabinoid isomers were synthesized and tested for pyschotropic activity in rhesus monkeys. Two regularities were observed: (a) In the absence of the other substituents, the equatorial stereochemistry of the substituent at C-1 determines activity, (b) Two groups of THC-type cannabinoids which differ only in that the chemical groupings in one of them at C-1, C-2 are situated at C-1, C-6 in the other (but retain their stereochemistry) have almost equivalent pyschotropic activity.

Original language	English
Pages (from-to)	1068-1072
Number of pages	5
Journal	Journal of Medicinal Chemistry
Volume	23
Issue number	10
DOIs	https://doi.org/10.1021/jm00184a002
State	Published - 1 Oct 1980
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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10.1021/jm00184a002

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abstract = "Several pairs of cannabinoid isomers were synthesized and tested for pyschotropic activity in rhesus monkeys. Two regularities were observed: (a) In the absence of the other substituents, the equatorial stereochemistry of the substituent at C-1 determines activity, (b) Two groups of THC-type cannabinoids which differ only in that the chemical groupings in one of them at C-1, C-2 are situated at C-1, C-6 in the other (but retain their stereochemistry) have almost equivalent pyschotropic activity.",

author = "R. Mechoulam and N. Lander and Varkony, {T. H.} and I. Kimmel and O. Becker and Z. Ben-Zvi and H. Edery and G. Porath",

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AU - Mechoulam, R.

AU - Lander, N.

AU - Varkony, T. H.

AU - Kimmel, I.

AU - Becker, O.

AU - Ben-Zvi, Z.

AU - Edery, H.

AU - Porath, G.

PY - 1980/10/1

Y1 - 1980/10/1

N2 - Several pairs of cannabinoid isomers were synthesized and tested for pyschotropic activity in rhesus monkeys. Two regularities were observed: (a) In the absence of the other substituents, the equatorial stereochemistry of the substituent at C-1 determines activity, (b) Two groups of THC-type cannabinoids which differ only in that the chemical groupings in one of them at C-1, C-2 are situated at C-1, C-6 in the other (but retain their stereochemistry) have almost equivalent pyschotropic activity.

AB - Several pairs of cannabinoid isomers were synthesized and tested for pyschotropic activity in rhesus monkeys. Two regularities were observed: (a) In the absence of the other substituents, the equatorial stereochemistry of the substituent at C-1 determines activity, (b) Two groups of THC-type cannabinoids which differ only in that the chemical groupings in one of them at C-1, C-2 are situated at C-1, C-6 in the other (but retain their stereochemistry) have almost equivalent pyschotropic activity.

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JO - Journal of Medicinal Chemistry

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IS - 10

ER -

Stereochemical Requirements for Cannabinoid Activity

Abstract

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