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Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens

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Ross, Ruth A, Gibson, T Michael, Brockie, Heather C, Leslie, Mark, Pashmi, Ghazaleh, Craib, Susan J, Di Marzo, Vincenzo, Pertwee, Roger G·2001·British Journal of Pharmacology

DOI 10.1038/sj.bjp.0703850PMC PMC1572597

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Abstract

1. This study was directed at exploring the structure-activity relationship for anandamide and certain of its analogues at the rat VR1 receptor in transfected cells and at investigating the relative extent to which anandamide interacts with CB(1) and vanilloid receptors in the mouse vas deferens. 2. pK(i) values for displacement of [(3)H]-resiniferatoxin from membranes of rVR1 transfected CHO cells were significantly less for anandamide (5.78) than for its structural analogues N-(4-hydroxyphenyl)-arachidonylamide (AM404; 6.18) and N-(3-methoxy-4-hydroxy)benzyl-arachidonylamide (arvanil; 6.77). 3. pEC(50) values for stimulating (45)Ca(2+) uptake into rVR1 transfected CHO cells were significantly less for anandamide (5.80) than for AM404 (6.32) or arvanil (9.29). Arvanil was also significantly more potent than capsaicin (pEC(50)=7.37), a compound with the same substituted benzyl polar head group as arvanil. 4. In the mouse vas deferens, resiniferatoxin was 218 times more potent than capsaicin as an inhibitor of electrically-evoked contractions. Both drugs were antagonized to a similar extent by capsazepine (pK(B)=6.93 and 7.18 respectively) but were not antagonized by SR141716A (1 microM). Anandamide was less susceptible than capsaicin to antagonism by capsazepine (pK(B)=6.02) and less susceptible to antagonism by SR141716A (pK(B)=8.66) than methanandamide (pK(B)=9.56). WIN55212 was antagonized by SR141716A (pK(B)=9.02) but not by capsazepine (10 microM). 5. In conclusion, anandamide and certain of its analogues have affinity and efficacy at the rat VR1 receptor. In the mouse vas deferens, which seems to express vanilloid and CB(1) receptors, both receptor types appear to contribute to anandamide-induced inhibition of evoked contractions.

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Background
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BackgroundInfluential
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Marzo, O. V. D., PETROCELLIS, L. D., & Bisogno, T. (2001) · Emerging Therapeutic Targets · doi:10.1517/14728222.5.2.241 · Cited by 27
Anticonvulsant Effects ofN‐Arachidonoyl‐Serotonin, a Dual Fatty Acid Amide Hydrolase Enzyme and Transient Receptor Potential Vanilloid Type‐1 ( TRPV 1) Channel Blocker, on Experimental Seizures: The Roles of Cannabinoid CB 1 Receptors and TRPV 1 Channels
Vilela, L., Medeiros, D. D. C., de Oliveira, A. C. P., Moraes, M. F. D., & Moreira, F. A. (2014) · Basic & Clinical Pharmacology & Toxicology · doi:10.1111/bcpt.12232 · Cited by 26
Big conductance calcium‐activated potassium channel openers control spasticity without sedation
Baker, D., Pryce, G., Visintin, C., Sisay, S., Bondarenko, A. I., Ho, W. ‐. V., Jackson, S. J., Williams, T. E., Al‐Izki, S., Sevastou, I. G., et al. (2017) · British Journal of Pharmacology · doi:10.1111/bph.13889 · Cited by 26
“, 2001) This is a standard, tissue-based assay used to detect cannabinoid receptor activity (Ross et al., 2001) but assesses autonomic neurotransmission for a wide range of receptors, via actions on nerves originating from pelvic and lumbar/sacral ganglia (Burnstock and Verkhratsky, 2010).”
BackgroundMethodInfluential
n−3 polyunsaturated N-acylethanolamines are CB2 cannabinoid receptor-preferring endocannabinoids
Alharthi, N. S., Christensen, P. S., Hourani, W., Ortori, C. A., Barrett, D. A., Bennett, A. J., Chapman, V., & Alexander, S. P. H. (2018) · Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids · doi:10.1016/j.bbalip.2018.08.003 · Cited by 28
Stimulation of epithelial CB1 receptors inhibits contractions of the rat prostate gland
Tokanovic, S., Malone, D. T., & Ventura, S. (2006) · British Journal of Pharmacology · doi:10.1038/sj.bjp.0706952 · Cited by 26
“However in this study, the chosen cannabinoid agonist WIN 55,212-2 lacks efficacy at the TRPV1 receptor avoiding conflicting results which may result using an endogenous cannabinoid such as anandamide (Zygmunt et al., 1999; Smart et al., 2000; Ross et al., 2001).”
Background
Neonatal anandamide treatment results in prolonged mitochondrial damage in the vanilloid receptor type 1-immunoreactive B-type neurons of the rat trigeminal ganglion
Szőke, É., Czéh, G., Szolcsányi, J., & Seress, L. (2002) · Neuroscience · doi:10.1016/s0306-4522(02)00420-7 · Cited by 26
Assay of TRPV1 Receptor Signaling
Moriello, A. S., & PETROCELLIS, L. D. (2016) · Methods in molecular biology · doi:10.1007/978-1-4939-3539-0_7 · Cited by 25
Analgesic, anti-inflammatory, and anti-pyretic activity1
Vogel, H. G., Vogel, W. H., Schölkens, B. A., Sandow, J., Müller, G. A., & Vogel, W. F. (2002) · Springer eBooks · doi:10.1007/3-540-29837-1_9 · Cited by 25
AM404 decreases Fos-immunoreactivity in the spinal cord in a model of inflammatory pain
Borsani, E., Labanca, M., Bianchi, R., & Rodella, L. F. (2007) · Brain Research · doi:10.1016/j.brainres.2007.03.071 · Cited by 25
AM404 inhibits NFAT and NF-κB signaling pathways and impairs migration and invasiveness of neuroblastoma cells
Caballero, F. J., Soler-Torronteras, R., Lara‐Chica, M., García, V., Fiebich, B. L., Muñóz, E., & Calzado, M. A. (2014) · European Journal of Pharmacology · doi:10.1016/j.ejphar.2014.11.023 · Cited by 25
Transient receptor potential vanilloid 1 channels modulate the anxiolytic effect of diazepam
Manna, S. S. S., & Umathe, S. N. (2011) · Brain Research · doi:10.1016/j.brainres.2011.09.049 · Cited by 23
Therapeutic applicability of cannabidiol and other phytocannabinoids in epilepsy, multiple sclerosis and Parkinson's disease and in comorbidity with psychiatric disorders
Sampaio, M. D. F. D. S., de Paiva, Y. B., Sampaio, T. B., Pereira, M. G., & Coimbra, N. C. (2024) · Basic & Clinical Pharmacology & Toxicology · doi:10.1111/bcpt.13997 · Cited by 28
“81,86,87 88 – 90 5-HT 1A is a serotonin receptor coupled to a Gi/o protein and has been related to cannabinoids antiaversive and other medical effects, including its neuroprotective effects.”
Background
The group IV afferent neuron expresses multiple receptor alterations in cardiomyopathyic rats: evidence at the cannabinoid CB1receptor
Williams, M. A., Smith, S. A., O’Brien, D. E., Mitchell, J. H., & Garry, M. G. (2007) · The Journal of Physiology · doi:10.1113/jphysiol.2007.140392 · Cited by 22
“Multiple defects occur on primary afferent neurons in cardiomyopathic rats CB1 receptors are present on group IV primary afferent fibres (Ross et al. 2001a,b) and are co-expressed with TRPv1 receptors (Ahluwalia et al. 2000, 2002, 2003; Bridges et al. 2003; Sagar et al. 2004).”
Background
Exploiting cannabinoid and vanilloid mechanisms for epilepsy treatment
Asth, L., Iglesias, L. P., de Oliveira, A. C., Moraes, M. F. D., & Moreira, F. A. (2019) · Epilepsy & Behavior · doi:10.1016/j.yebeh.2019.106832 · Cited by 25
Assessment of clinical outcomes in patients with fibromyalgia: Analysis from the UK Medical Cannabis Registry
Wang, C., Erridge, S., Holvey, C., Coomber, R., Usmani, A., Sajad, M., Guru, R., Holden, W., Rucker, J., Platt, M. W., et al. (2023) · Brain and Behavior · doi:10.1002/brb3.3072 · Cited by 22
“Anandamide is also a TRPV1 agonist with high binding affinity but a reduced activating effect (Lizanecz et al., 2006; Ross et al., 2001).”
Background
AKAP150-Mediated TRPV1 Sensitization is Disrupted by Calcium/Calmodulin
Chaudhury, S., Bal, M., Belugin, S., Shapiro, M. S., & Jeske, N. A. (2011) · Molecular Pain · doi:10.1186/1744-8069-7-34 · Cited by 21
“TRPV1 participates in physical and chemical pain-evoked signal transduction, as it is activated by capsaicin, noxious heat (>42°C, [2]), low pH [4], cannabinoids including anandamide [5, 6 ], and certain lipids [7].”
Background
The prefrontal cortical endocannabinoid system modulates fear–pain interactions in a subregion‐specific manner
Rea, K., McGowan, F., Corcoran, L., Roche, M., & Finn, D. P. (2018) · British Journal of Pharmacology · doi:10.1111/bph.14376 · Cited by 22
“, 2000; Petrosino and Di Marzo, 2017), TRPV1 channels (Smart et al., 2000; De Petrocellis et al., 2001; Di Marzo et al., 2001; Ross et al., 2001), PPARs (LoVerme et al.”
Background
AM404 enhances the spontaneous release of l-glutamate in a manner sensitive to capsazepine in adult rat substantia gelatinosa neurones
Yue, H., Fujita, T., Kawasaki, Y., & Kumamoto, E. (2004) · Brain Research · doi:10.1016/j.brainres.2004.05.090 · Cited by 21
Biosynthesis of endocannabinoids and their modes of action in neurodegenerative diseases
van der Stelt, M., Hansen, H. H., Veldhuis, W. B., Bär, P. R., Nicolay, K., Veldink, G. A., Vliegenthart, J. F. G., & Hansen, H. S. (2003) · Neurotoxicity Research · doi:10.1007/bf03033139 · Cited by 21
“…anandamide, but not 2-AG, is considered being an endogenous activator of the ionotropic vanilloid VR 1 receptor (Zygmunt et al. , 1999), possibly activating the receptor from an intracellular binding domain following cellular uptake of anandamide (De Petrocellis et al. , 2001; Ross et al. , 2001).”
Endovanilloids are potential activators of the trigeminovascular nocisensor complex
Dux, M., Deák, É., Tassi, N., Sántha, P., & Jancsó, G. (2016) · The Journal of Headache and Pain · doi:10.1186/s10194-016-0644-7 · Cited by 20
“Several lines of evidence suggest that anandamide binds to the same binding site of the TRPV1 receptor as capsaicin [45].”
Background
Modifications of Capsaicin-Sensitive Neurons in Isolated Guinea Pig Ileum by [6]-Gingerol and Lafutidine
Someya, A., Horie, S., Yamamoto, H., & Murayama, T. (2003) · Journal of Pharmacological Sciences · doi:10.1254/jphs.92.359 · Cited by 18
Potential Mechanisms Involved in Palmitoylethanolamide-Induced Vasodepressor Effects in Rats
Marichal‐Cancino, B. A., González‐Hernández, A., MaassenVanDenBrink, A., Juan, E. R., & Villalón, C. M. (2020) · Journal of Vascular Research · doi:10.1159/000506158 · Cited by 17
Analgesic, Anti-inflammatory, and Anti-pyretic Activity
Vogel, H. G. (2007) · Springer eBooks · doi:10.1007/978-3-540-70995-4_9 · Cited by 18
Methanandamide Hyperpolarizes Gastric Arteries by Stimulation of TRPV1 Receptors on Perivascular CGRP Containing Nerves
Breyne, J., & Vanheel, B. (2006) · Journal of Cardiovascular Pharmacology · doi:10.1097/01.fjc.0000205053.53946.10 · Cited by 17
“This hyperpolarization is due to activation of KATP channels of the vascular smooth muscle cells and the response is mimicked by exogenous CGRP.”
BackgroundInfluential
Modification of TRPV4 activity by acetaminophen
Nakagawa, F., Higashi, S., Ando, E., Ohsumi, T., Watanabe, S., & Takeuchi, H. (2020) · Heliyon · doi:10.1016/j.heliyon.2020.e03301 · Cited by 16
Effects of chronic nitric oxide synthase inhibition on the cardiovascular responses to cannabinoids in vivo and in vitro
Wheal, A. J., Bennett, T. M., Randall, M. D., & Gardiner, S. M. (2007) · British Journal of Pharmacology · doi:10.1038/sj.bjp.0707136 · Cited by 15
“…than in ethanol in vitro (W-S V Ho, unpublished observations), and the effect of methanandamide at TRPV1 receptors is lower than anandamide (Ross et al., 2001), it is possible that in our experiments using methanandamide in Tocrisolve, we were below the threshold for activation of TRPV1…”
Activation of the capsaicin-receptor TRPV1 by the acetaminophen metabolite N -arachidonoylaminophenol results in cytotoxicity
Stueber, T., Meyer, S., Jangra, A., Hage, A., Eberhardt, M., & Leffler, A. (2018) · Life Sciences · doi:10.1016/j.lfs.2017.12.024 · Cited by 16
Mammalian Fatty Acid Amides of the Brain and CNS
Waluk, D. P., Battistini, M. R., Dempsey, D. R., Farrell, E. K., Jeffries, K. A., Mitchell, P. R., Hernandez, L. W., McBride, J. C., Merkler, D. J., & Hunt, M. C. (2014) · Elsevier eBooks · doi:10.1016/b978-0-12-410527-0.00009-0 · Cited by 18
The State of Synthetic Cannabinoid Medications for the Treatment of Pain
Maglaviceanu, A., Peer, M., Rockel, J. S., Bonin, R. P., Fitzcharles, M., Ladha, K. S., Bhatia, A., Leroux, T. S., Kotra, L. P., Kapoor, M., et al. (2024) · CNS Drugs · doi:10.1007/s40263-024-01098-9 · Cited by 14
N-Morpholino- and N-diethyl-analogues of palmitoylethanolamide increase the sensitivity of transfected human vanilloid receptors to activation by anandamide without affecting fatty acid amidohydrolase activity
Vandevoorde, S., Lambert, D. M., Smart, D., Jonsson, K., & Fowler, C. J. (2003) · Bioorganic & Medicinal Chemistry · doi:10.1016/s0968-0896(02)00567-9 · Cited by 13
TRPV1 Activation by Anandamide via a Unique Lipid Pathway
Muller, C., Lynch, D. L., Hurst, D. P., & Reggio, P. H. (2021) · Journal of Chemical Information and Modeling · doi:10.1021/acs.jcim.1c00893 · Cited by 12
Effects of cannabinoids on capsaicin receptor activity following exposure of primary sensory neurons to inflammatory mediators
Soneji, N. D. R., Paule, C. C., Mlynarczyk, M., & Nagy, I. (2010) · Life Sciences · doi:10.1016/j.lfs.2010.06.003 · Cited by 12
Therapeutic Targeting of Peripheral Cannabinoid Receptors in Inflammatory and Neuropathic Pain States
Spigelman, I. (2009) · Frontiers in neuroscience · doi:10.1201/9781439812105-c5 · Cited by 12
Chapter 13 Endogenous Cannabinoids and Neutrophil Chemotaxis
McHugh, D., & Ross, R. A. (2009) · Vitamins and hormones · doi:10.1016/s0083-6729(09)81013-3 · Cited by 11
Role of Pre‐Junctional CB 1, But not CB 2, TRPV 1 or GPR 55 Receptors in Anandamide‐Induced Inhibition of the Vasodepressor Sensory CGRP ergic Outflow in Pithed Rats
Marichal‐Cancino, B. A., Altamirano‐Espinoza, A. H., Manrique‐Maldonado, G., MaassenVanDenBrink, A., & Villalón, C. M. (2013) · Basic & Clinical Pharmacology & Toxicology · doi:10.1111/bcpt.12152 · Cited by 10
Expression of functional TRPV 1 receptor in primary culture of canine keratinocytes
Barbero, R., Vercelli, C., Cuniberti, B., della Valle, M. F., Martano, M., & Re, G. (2018) · Journal of Veterinary Pharmacology and Therapeutics · doi:10.1111/jvp.12694 · Cited by 11
Cannabinoids in neuropathic pain treatment: pharmacological insights and clinical outcomes from recent trials
Khan, M. G., Hussain, S. H. A., Alkhayl, F. F. A., Ahsan, M., & Ridha‐Salman, H. (2025) · Naunyn-Schmiedeberg s Archives of Pharmacology · doi:10.1007/s00210-025-04134-7 · Cited by 10
“In addition, endocannabinoids interact with non-cannabi-noid receptors in the brain, such as transient receptor potential vanilloid type 1 (TRPV1) channel (Ross et al. 2001) and peroxisome proliferator-activated receptor-ϒ (PPAR-ϒ ) (Bouaboula et al. 2005).”
Non-CB1, Non-CB2 Receptors for Endocannabinoids
PETROCELLIS, L. D., & Marzo, V. D. (2005) · CRC Press eBooks · doi:10.1201/9781420023640.ch6 · Cited by 9
Blockade of Cannabinoid CB1 Receptors in the Dorsal Periaqueductal Gray Unmasks the Antinociceptive Effect of Local Injections of Anandamide in Mice
Mascarenhas, D. C., Gomes, K. S., Sorregotti, T., & Nunes‐de‐Souza, R. L. (2017) · Frontiers in Pharmacology · doi:10.3389/fphar.2017.00695 · Cited by 8
“In this context, in terms of pharmacodynamics, AEA binds to CB1 Frontiers in Pharmacology | www.frontiersin.org 8 October 2017 | Volume 8 | Article 695 receptors with higher affinity (Ki value between 37 and 116 nM) compared to TRPV1 receptor (Ki value 1.66 µM) (Ross et al., 2001).”
BackgroundInfluential
Role of VR1 and CB1 receptors in modelling of cardio-respiratory response to arvanil, an endocannabinoid and vanilloid hybrid, in rats
Kopczyńska, B. (2008) · Life Sciences · doi:10.1016/j.lfs.2008.04.023 · Cited by 7
Inhibition of Adult Neurogenesis in Male Mice after Repeated Exposure to Paracetamol Overdose
Suárez, J., de Ceglia, M., Rodríguez-Pozo, M., Vargas, A., Santos, I., Melgar‐Locatelli, S., Castro‐Zavala, A., Castilla‐Ortega, E., de Fonseca, F. R., Decara, J. M., et al. (2024) · International Journal of Molecular Sciences · doi:10.3390/ijms25041964 · Cited by 5
“Animal studies comply with the ARRIVE guidelines.”
The Hippocampal Endocannabinoid System in Different Memory Phases: Unveiling the CA1 Circuitry
Quillfeldt, J. A., & Alvares, L. D. O. (2015) · Springer eBooks · doi:10.1007/978-1-4939-2294-9_3 · Cited by 7
High-Fat Diet-Induced Insulin Resistance Does Not Increase Plasma Anandamide Levels or Potentiate Anandamide Insulinotropic Effect in Isolated Canine Islets
Woolcott, O. O., Richey, J. M., Kabir, M., Chow, R. H.-P., Iyer, M. S., Kirkman, E. L., Stefanovski, D., Lottati, M., Kim, S. P., Harrison, L. N., et al. (2015) · PLoS ONE · doi:10.1371/journal.pone.0123558 · Cited by 6
The use of cannabinoids in multiple sclerosis
Teare, L., & Zajicek, J. (2005) · Expert Opinion on Investigational Drugs · doi:10.1517/13543784.14.7.859 · Cited by 6
“Anandamide has lower relative intrinsic activity than capsaicin at vanilloid receptors [29] and activates VR1 receptors at concentrations of 10 – 20-fold higher than the concentration at which it activates CB1 receptors [30].”
Background
Occurrence, Biosynthesis, and Metabolism of Endocannabinoids
Waku, K., Ikeda, S., Sugiura, T., & Oka, S. (2005) · CRC Press eBooks · doi:10.1201/9781420023640.pt3 · Cited by 6
Dual effects of anandamide in the antiepileptic activity of diazepam in pentylenetetrazole-induced seizures in mice
Manna, S. S. S. (2022) · Behavioural Pharmacology · doi:10.1097/fbp.0000000000000700 · Cited by 5
“Interestingly, AEA, an endogenous agonist of CB 1 receptor also activates the TRPV1 (Zygmunt et al., 1999; Ross et al., 2001; Smart et al., 2002).”
Background
The Endocannabinoid System as a Target for New Antiseizure Drugs
Vilela, L., de Oliveira, A. C. P., Moraes, M. F. D., Moreira, F. A., & Takahashi, R. N. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-800756-3.00073-9 · Cited by 5
Blockade of the endovanilloid receptor, TRPV1, and of the endocannabinoid enzyme, FAAH, within the nucleus accumbens shell elicits anxiolytic-like effects in male rats
Pardo-García, T. R., Yusif-Rodriguez, N., Yudowski, G. A., & Maldonado-Vlaar, C. S. (2020) · Neuroscience Letters · doi:10.1016/j.neulet.2020.135023 · Cited by 4
Preclinical Pharmacological and Brain Bioassay Systems for CB1 Cannabinoid Receptors
Wiley, J. L., & Martin, B. R. (2008) · Humana Press eBooks · doi:10.1007/978-1-59745-503-9_12 · Cited by 4
“[139] assessed TRPV1 receptor binding directly through displacement of the radiolabeled TRPV1 agonist, [ H]resiniferatoxin, in CHO cells expressing TRPV1 receptors.”
Background
Endocannabinoids Part II: pathological CNS conditions involving the endocannabinoid system and their possible treatment with endocannabinoid-based drugs
Marzo, V. D., Bisogno, T., & PETROCELLIS, L. D. (2001) · Expert Opinion on Therapeutic Targets · doi:10.1517/14728222.5.3.349 · Cited by 4
“However, AM404 is also a potent agonist at the vanilloid VR1 receptors [19], which are blocked by high concentrations of SR141716A [20].”
Background

Authors: Ross, R. A., Gibson, T. M., Brockie, H. C., Leslie, M., Pashmi, G., Craib, S. J., Di Marzo, V., & Pertwee, R. G.
Affiliations: University of Aberdeen (GB)
Corresponding author: Ross, Ruth A
ORCID: Ross, Ruth A
Pertwee, Roger G
Venue: British Journal of Pharmacology
Publisher: Wiley
Published: 2001-02
Volume: 132
Issue: 3
Pages: 631-640
ISSN: 0007-1188 (ISSN-L)
1476-5381
DOI: 10.1038/sj.bjp.0703850
PMC: PMC1572597
OpenAlex: W2021876302
Cited by: 237
References: 28
Citations by year: 2026: 3 · 2025: 1 · 2024: 6 · 2023: 2 · 2022: 1 · 2021: 1 · 2020: 4 · 2019: 2 · 2018: 6 · 2017: 8 · 2016: 4 · 2015: 12 · 2014: 6 · 2013: 12 · 2012: 6
FWCI: 9.89
Type: journal article
Language: en
Open access: bronze
doi.org
Licence: onlinelibrary.wiley.com/termsAndConditions#vor (vor, 2919 d)
Locations: British Journal of Pharmacology (publishedVersion)
PubMed Central (publishedVersion)
PubMed (publishedVersion)
Funders: Wellcome Trust
National Institute on Drug Abuse (P01DA009789, DA 09789)
Topics: Life Sciences › Neuroscience › Sensory Systems › Ion Channels and Receptors
Health Sciences › Medicine › Pharmacology (medical) › Cannabis and Cannabinoid Research
Health Sciences › Medicine › Physiology (medical) › Pain Mechanisms and Treatments
Keywords: anandamide, structure-activity relationship, vanilloid receptor 1, CB1 receptor, cannabinoid analogues, AM404, resiniferatoxin, capsaicin, vas deferens contraction, SR141716A, capsazepine, methanandamide, receptor binding affinity
MeSH terms: Rimonabant, Animals, Arachidonic Acids, Binding, Competitive, Biological Transport, Calcium, Calcium Channel Blockers, Cannabinoids, Capsaicin, Drug Interactions, Electric Stimulation, Enzyme Inhibitors, Cricetinae, Male, Morpholines, Muscle Contraction, Naphthalenes, Phenylmethylsulfonyl Fluoride, Piperidines, Pyrazoles, Radioligand Assay, Receptors, Drug, Structure-Activity Relationship, Transfection, Vas Deferens, CHO Cells, Receptors, Cannabinoid, Benzoxazines, TRPV Cation Channels, Mice, Polyunsaturated Alkamides, Endocannabinoids

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Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens

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