Cited by 2,913Cannabis and Cannabinoid ResearchFatty Acid Research and HealthEicosanoids and Hypertension Pharmacology

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Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors

Mechoulam, Raphael, Ben-Shabat, Shimon, Hanus, Lumir, Ligumsky, Moshe, Kaminski, Norbert E., Schatz, Anthony R., Gopher, Asher, Almog, Shlomo, Martin, Billy R., Compton, David R., Pertwee, Roger G., Griffin, Graeme, Bayewitch, Michael, Barg, Jacob, Vogel, Zvi·1995·Biochemical Pharmacology

DOI 10.1016/0006-2952(95)00109-d

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Abstract

In this study, we report the isolation from canine intestines of 2-arachidonyl glycerol (2-Ara-Gl). Its structure was determined by mass spectrometry and by direct comparison with a synthetic sample. 2-Ara-Gl bound to membranes from cells transiently transfected with expression plasmids carrying DNA of either CB1 or CB2--the two cannabinoid receptors identified thus far--with Ki values of 472 +/- 55 and 1400 +/- 172 nM, respectively. In the presence of forskolin, 2-Ara-Gl inhibited adenylate cyclase in isolated mouse spleen cells, at the potency level of delta 9-tetrahydrocannabinol (delta 9-THC). Upon intravenous administration to mice, 2-Ara-Gl caused the typical tetrad of effects produced by THC: antinociception, immobility, reduction of spontaneous activity, and lowering of the rectal temperature. 2-Ara-Gl also shares the ability of delta 9-THC to inhibit electrically evoked contractions of mouse isolated vasa deferentia; however, it was less potent than delta 9-THC.

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“These receptors, as well as the endogenous cannabinoids (endocannabinoids) 2-arachidonoylglycerol (2-AG; Mechoulam et al., 1995; Sugiura et al., 1995) and N-arachidonoylethanolamine”
Background
Modulation of anxiety-like behavior by the endocannabinoid 2-arachidonoylglycerol (2-AG) in the dorsolateral periaqueductal gray
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Authors: Mechoulam, R., Ben-Shabat, S., Hanus, L., Ligumsky, M., Kaminski, N. E., Schatz, A. R., Gopher, A., Almog, S., Martin, B. R., Compton, D. R., Pertwee, R. G., Griffin, G., Bayewitch, M., Barg, J., & Vogel, Z.
Affiliations: Hebrew University of Jerusalem (IL)
Michigan State University (US)
Virginia Commonwealth University (US)
Sheba Medical Center (IL)
University of Aberdeen (GB)
Weizmann Institute of Science (IL)
Corresponding author: Mechoulam, Raphael
ORCID: Mechoulam, Raphael
Hanus, Lumir
Kaminski, Norbert E.
Gopher, Asher
Pertwee, Roger G.
Venue: Biochemical Pharmacology
Publisher: Elsevier BV
Published: 1995-06
Volume: 50
Issue: 1
Pages: 83-90
ISSN: 0006-2952 (ISSN-L)
DOI: 10.1016/0006-2952(95)00109-d
OpenAlex: W2024653583
Cited by: 2,913
References: 42
Citations by year: 2026: 27 · 2025: 69 · 2024: 89 · 2023: 84 · 2022: 103 · 2021: 125 · 2020: 118 · 2019: 110 · 2018: 89 · 2017: 105 · 2016: 112 · 2015: 109 · 2014: 98 · 2013: 104 · 2012: 137
FWCI: 22.43
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
Locations: Biochemical Pharmacology (publishedVersion)
PubMed (publishedVersion)
Funders: Wellcome Trust
National Institutes of Health (5r01da008169-02)
U.S. Public Health Service
National Institute on Drug Abuse (DA 8169, DA-3672)
Topics: Health Sciences › Medicine › Pharmacology (medical) › Cannabis and Cannabinoid Research
Health Sciences › Nursing › Nutrition and Dietetics › Fatty Acid Research and Health
Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Eicosanoids and Hypertension Pharmacology
Keywords: 2-arachidonoylglycerol, endocannabinoids, cannabinoid receptors, CB1 receptor, CB2 receptor, canine intestine, adenylate cyclase inhibition, forskolin, delta-9-tetrahydrocannabinol, antinociception, immobility, hypothermia, vas deferens contraction, structure elucidation
MeSH terms: Animals, Arachidonic Acids, Cannabinoids, Cell Line, Dogs, Glycerides, Intestines, Male, Gas Chromatography-Mass Spectrometry, Mice, Inbred ICR, Receptors, Drug, Molecular Structure, Receptors, Cannabinoid, Mice, Endocannabinoids

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Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors

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