M320 (opioid)

M320 (opioid)
Clinical data
Other names	(5α,6β,14β,18R)-17-(Cyclopropylmethyl)-18-[(2R)-2-hydroxy-5-methyl-2-hexanyl]-6-methoxy-7,8-didehydro-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol
ATC code	none;
Legal status
Legal status	UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name (1R,2S,6R,14R,15R,19R)-5-(Cyclopropylmethyl)-19-[(2R)-2-hydroxy-5-methylhexan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11,16-tetraen-11-ol;
PubChem CID	71717732;
ChemSpider	29420445;
ChEMBL	ChEMBL2338714;
Chemical and physical data
Formula	C30H41NO4
Molar mass	479.661 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)CC[C@](C)([C@H]1C[C@@]23C=C[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O;
	InChI InChI=1S/C30H41NO4/c1-18(2)9-10-27(3,33)22-16-28-11-12-30(22,34-4)26-29(28)13-14-31(17-19-5-6-19)23(28)15-20-7-8-21(32)25(35-26)24(20)29/h7-8,11-12,18-19,22-23,26,32-33H,5-6,9-10,13-17H2,1-4H3/t22-,23-,26-,27-,28-,29+,30-/m1/s1; Key:MFIWLPVODKSMKX-XELDOGJXSA-N;

M320 is an extremely potent and long acting opioid. It produces long lasting narcosis in different animals, including mice, rats, cats, guinea pigs, dogs and monkeys.^[1] M320 is a μ and κ-opioid receptor agonist.^[2]^[3]^[4]

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[1]
Boura AL, Fitzgerald AE (February 1966). "The pharmacology of N-(cyclopropylmethyl)-19-isopentylnororvinol hydrochloride. A potent and long lasting central depressant". British Journal of Pharmacology and Chemotherapy. 26 (2): 307–321. doi:10.1111/j.1476-5381.1966.tb01910.x. PMC 1510649. PMID 4958020.
[2]
Abrahams JM, Boura AL, Evans RG, Johnston CI, Olley JE (December 1986). "The effects of N-(cyclopropylmethyl)-19-isopentylnororvinol (M320), a potent agonist at kappa- and mu-opiate receptors, on urine excretion of rats". British Journal of Pharmacology. 89 (4): 759–767. doi:10.1111/j.1476-5381.1986.tb11180.x. PMC 1917223. PMID 3028550.
[3]
Evans RG, Rice GE, Olley JE (November 1988). "Studies of the effects of subacute treatment with N-(cyclopropylmethyl)-19-isopentylnororvinol (M320) on timing of parturition in the rat". British Journal of Pharmacology. 95 (3): 777–782. doi:10.1111/j.1476-5381.1988.tb11704.x. PMC 1854236. PMID 3207993.
[4]
Greedy BM, Bradbury F, Thomas MP, Grivas K, Cami-Kobeci G, Archambeau A, et al. (April 2013). "Orvinols with mixed kappa/mu opioid receptor agonist activity". Journal of Medicinal Chemistry. 56 (8): 3207–3216. doi:10.1021/jm301543e. PMC 3646402. PMID 23438330.

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[bjp-1] [1]
Boura AL, Fitzgerald AE (February 1966). "The pharmacology of N-(cyclopropylmethyl)-19-isopentylnororvinol hydrochloride. A potent and long lasting central depressant". British Journal of Pharmacology and Chemotherapy. 26 (2): 307–321. doi:10.1111/j.1476-5381.1966.tb01910.x. PMC 1510649. PMID 4958020.

[bjp2-2] [2]
Abrahams JM, Boura AL, Evans RG, Johnston CI, Olley JE (December 1986). "The effects of N-(cyclopropylmethyl)-19-isopentylnororvinol (M320), a potent agonist at kappa- and mu-opiate receptors, on urine excretion of rats". British Journal of Pharmacology. 89 (4): 759–767. doi:10.1111/j.1476-5381.1986.tb11180.x. PMC 1917223. PMID 3028550.

[bjp3-3] [3]
Evans RG, Rice GE, Olley JE (November 1988). "Studies of the effects of subacute treatment with N-(cyclopropylmethyl)-19-isopentylnororvinol (M320) on timing of parturition in the rat". British Journal of Pharmacology. 95 (3): 777–782. doi:10.1111/j.1476-5381.1988.tb11704.x. PMC 1854236. PMID 3207993.

[4] [4]
Greedy BM, Bradbury F, Thomas MP, Grivas K, Cami-Kobeci G, Archambeau A, et al. (April 2013). "Orvinols with mixed kappa/mu opioid receptor agonist activity". Journal of Medicinal Chemistry. 56 (8): 3207–3216. doi:10.1021/jm301543e. PMC 3646402. PMID 23438330.

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M320 (opioid)

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