IDENTIFICATION OF AN ENDOGENOUS 2-MONOGLYCERIDE, PRESENT IN CANINE GUT, THAT BINDS TO CANNABINOID RECEPTORS

R MECHOULAM, S BENSHABAT, L HANUS, M LIGUMSKY, N E KAMINSKI, A R SCHATZ, A GOPHER, S ALMOG, D R COMPTON, Roger Guy Pertwee, G GRIFFIN, M BAYEWITCH, J BARG, Z VOGEL, Billy R. Martin

Research output: Contribution to journalArticle

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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 K-i 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.

Original languageEnglish
Pages (from-to)83-90
Number of pages8
JournalBiochemical Pharmacology
Volume50
Issue number1
DOIs
Publication statusPublished - 29 Jun 1995

Keywords

  • 2-ARACHIDONYL GLYCEROL
  • ANAND AMIDE
  • TETRAHYDROCANNABINOL
  • ARACHIDONYLETHANOLAMIDE
  • IMMUNE SYSTEM
  • TRANSFECTION
  • MOUSE BEHAVIOR
  • ADENYLATE CYCLASE INHIBITION
  • MOUSE SPLEEN-CELLS
  • CANNABIMIMETIC AGENTS
  • BRAIN CONSTITUENT
  • ADENYLATE-CYCLASE
  • ANANDAMIDE
  • DELTA-9-TETRAHYDROCANNABINOL
  • EXPRESSION
  • INHIBITION
  • AGONIST
  • 2-arachidonyl glycerol
  • tetrahydrocannabinol
  • anandamide
  • arachidonylethanolamide
  • immune system
  • transfection
  • mouse behavior
  • adenylate cyclase inhibition

Cite this

MECHOULAM, R., BENSHABAT, S., HANUS, L., LIGUMSKY, M., KAMINSKI, N. E., SCHATZ, A. R., ... Martin, B. R. (1995). IDENTIFICATION OF AN ENDOGENOUS 2-MONOGLYCERIDE, PRESENT IN CANINE GUT, THAT BINDS TO CANNABINOID RECEPTORS. Biochemical Pharmacology, 50(1), 83-90. https://doi.org/10.1016/0006-2952(95)00109-D

IDENTIFICATION OF AN ENDOGENOUS 2-MONOGLYCERIDE, PRESENT IN CANINE GUT, THAT BINDS TO CANNABINOID RECEPTORS. / MECHOULAM, R ; BENSHABAT, S ; HANUS, L ; LIGUMSKY, M ; KAMINSKI, N E ; SCHATZ, A R ; GOPHER, A ; ALMOG, S ; COMPTON, D R ; Pertwee, Roger Guy; GRIFFIN, G ; BAYEWITCH, M ; BARG, J ; VOGEL, Z ; Martin, Billy R.

In: Biochemical Pharmacology, Vol. 50, No. 1, 29.06.1995, p. 83-90.

Research output: Contribution to journalArticle

MECHOULAM, R, BENSHABAT, S, HANUS, L, LIGUMSKY, M, KAMINSKI, NE, SCHATZ, AR, GOPHER, A, ALMOG, S, COMPTON, DR, Pertwee, RG, GRIFFIN, G, BAYEWITCH, M, BARG, J, VOGEL, Z & Martin, BR 1995, 'IDENTIFICATION OF AN ENDOGENOUS 2-MONOGLYCERIDE, PRESENT IN CANINE GUT, THAT BINDS TO CANNABINOID RECEPTORS', Biochemical Pharmacology, vol. 50, no. 1, pp. 83-90. https://doi.org/10.1016/0006-2952(95)00109-D
MECHOULAM, R ; BENSHABAT, S ; HANUS, L ; LIGUMSKY, M ; KAMINSKI, N E ; SCHATZ, A R ; GOPHER, A ; ALMOG, S ; COMPTON, D R ; Pertwee, Roger Guy ; GRIFFIN, G ; BAYEWITCH, M ; BARG, J ; VOGEL, Z ; Martin, Billy R. / IDENTIFICATION OF AN ENDOGENOUS 2-MONOGLYCERIDE, PRESENT IN CANINE GUT, THAT BINDS TO CANNABINOID RECEPTORS. In: Biochemical Pharmacology. 1995 ; Vol. 50, No. 1. pp. 83-90.
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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 K-i 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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T1 - IDENTIFICATION OF AN ENDOGENOUS 2-MONOGLYCERIDE, PRESENT IN CANINE GUT, THAT BINDS TO CANNABINOID RECEPTORS

AU - MECHOULAM, R

AU - BENSHABAT, S

AU - HANUS, L

AU - LIGUMSKY, M

AU - KAMINSKI, N E

AU - SCHATZ, A R

AU - GOPHER, A

AU - ALMOG, S

AU - COMPTON, D R

AU - Pertwee, Roger Guy

AU - GRIFFIN, G

AU - BAYEWITCH, M

AU - BARG, J

AU - VOGEL, Z

AU - Martin, Billy R.

PY - 1995/6/29

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N2 - 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 K-i 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.

AB - 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 K-i 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.

KW - 2-ARACHIDONYL GLYCEROL

KW - ANAND AMIDE

KW - TETRAHYDROCANNABINOL

KW - ARACHIDONYLETHANOLAMIDE

KW - IMMUNE SYSTEM

KW - TRANSFECTION

KW - MOUSE BEHAVIOR

KW - ADENYLATE CYCLASE INHIBITION

KW - MOUSE SPLEEN-CELLS

KW - CANNABIMIMETIC AGENTS

KW - BRAIN CONSTITUENT

KW - ADENYLATE-CYCLASE

KW - ANANDAMIDE

KW - DELTA-9-TETRAHYDROCANNABINOL

KW - EXPRESSION

KW - INHIBITION

KW - AGONIST

KW - 2-arachidonyl glycerol

KW - tetrahydrocannabinol

KW - anandamide

KW - arachidonylethanolamide

KW - immune system

KW - transfection

KW - mouse behavior

KW - adenylate cyclase inhibition

U2 - 10.1016/0006-2952(95)00109-D

DO - 10.1016/0006-2952(95)00109-D

M3 - Article

VL - 50

SP - 83

EP - 90

JO - Biochemical Pharmacology

JF - Biochemical Pharmacology

SN - 0006-2952

IS - 1

ER -