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{{Short description|Chemical compound}}
{{drugbox | verifiedrevid = 410808162
{{Drugbox
|
| Verifiedfields = changed
| IUPAC_name = 3,6α-dihydroxy- 4,5α-epoxy- 7,8-didehydromorphinan
| image = Normorphine.svg | Watchedfields = changed
| width = 180 | verifiedrevid = 412254473
| CAS_number = 466-97-7 | IUPAC_name = 3,6α-Dihydroxy-4,5α-epoxy-7,8-didehydromorphinan
| synonyms = Normorphine | image = Normorphine.svg
| ATC_prefix = none | width = 180
| ATC_suffix = <!--Clinical data-->| tradename =
| PubChem = 430245 | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | IUPHAR_ligand = 1630
| DrugBank = | pregnancy_category =
| C = 16 | H = 17 | N = 1 | O = 3 | legal_AU = S9
⚫ | legal_BR = A1
| molecular_weight = 271.311 g/mol
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
⚫ | bioavailability =
| protein_bound = | legal_CA = Schedule I
⚫ | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫ | metabolism =
| legal_US = Schedule I
| legal_DE = Anlage I
| dependency_liability = High
⚫ | routes_of_administration = <!--Pharmacokinetic data-->
⚫ | bioavailability =
⚫ | protein_bound =
| metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion = <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X --> | CAS_number = 466-97-7
| ATC_prefix = none
| pregnancy_category=
| ATC_suffix =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| PubChem = 5462508
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| DrugBank =
⚫ | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = Schedule I | KEGG = C11785
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫ | legal_status =
| ChemSpiderID = 4575435
⚫ | routes_of_administration =
⚫ | IUPHAR_ligand = 1630
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = XUI1Y24IMI
<!--Chemical data-->| C = 16
| H = 17
| N = 1
| O = 3
| ChEMBL = 1227
| synonyms = Normorphine
| smiles = c1cc(c2c3c1C453(CCN4)(O2)(C=C5)O)O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2/t9-,10+,12-,15-,16-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = ONBWJWYUHXVEJS-ZTYRTETDSA-N
}} }}


⚫ '''Normorphine''' is an ] analogue, the N-demethylated derivative of ], that was first described in the 1950s<ref>{{cite journal | vauthors = Clark RL, Pessolano AA, Weijlard J, Pfister K | title = N-Substituted epoxymorphinans | journal = Journal of the American Chemical Society | date = October 1953 | volume = 75 | issue = 20 | pages = 4963–7 | doi = 10.1021/ja01116a024 }}</ref> when a large group of N-substituted morphine analogues were characterized for activity. The compound has relatively little opioid activity in its own right,<ref>{{cite journal | vauthors = Fraser HF, Wikler A, Van Horn GD, Eisenman AJ, Isbell H | title = Human pharmacology and addiction liability of normorphine | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 122 | issue = 3 | pages = 359–69 | date = March 1958 | pmid = 13539761 }}</ref><ref>{{cite journal | vauthors = Lasagna L, De Kornfeld TJ | title = Analgesic potency of normorphine in patients with postoperative pain | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 124 | issue = 3 | pages = 260–3 | date = November 1958 | pmid = 13588540 }}</ref> but is a useful intermediate which can be used to produce both ]s such as ], and also potent opioid agonists such as ].<ref>{{cite journal | vauthors = Yeh SY | title = Urinary excretion of morphine and its metabolites in morphine-dependent subjects | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 192 | issue = 1 | pages = 201–10 | date = January 1975 | pmid = 235634 }}</ref> with its formation from morphine catalyzed by the ] ]s ] and ].<ref>{{cite journal | vauthors = Projean D, Morin PE, Tu TM, Ducharme J | title = Identification of CYP3A4 and CYP2C8 as the major cytochrome P450 s responsible for morphine N-demethylation in human liver microsomes | journal = Xenobiotica; the Fate of Foreign Compounds in Biological Systems | volume = 33 | issue = 8 | pages = 841–54 | date = August 2003 | pmid = 12936704 | doi = 10.1080/0049825031000121608 | s2cid = 41467595 }}</ref>
'''Normorphine''' is an ] analogue that is the N-demethylated derivative of ].


Normorphine is a controlled substance listed under the Single Convention On Narcotic Drugs 1961 and the laws in various states implementing it; for example, in the United States it is a Schedule I Narcotic controlled substance, with an ACSCN of 9313 and an annual aggregate manufacturing quota of 18 grams in 2014, unchanged from the prior year. The salts in use are the free base hexahydrate (free base conversion ratio 0.715), and hydrochloride (0.833).<ref>{{Cite web | url=http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm | title = Quotas - 2014 | work = DEA Diversion Control Division}}</ref>
⚫ Normorphine has relatively little opioid activity in its own right,<ref>Fraser HF, Wikler A, Van Horn GD, Eisenman AJ, Isbell H. Human pharmacology and addiction liability of normorphine. ''Journal of Pharmacology and Experimental Therapeutics''. 1958 Mar;122(3):359-69. PMID 13539761</ref><ref>Lasagna L, De Kornfeld TJ. Analgesic potency of normorphine in patients with postoperative pain. ''Journal of Pharmacology and Experimental Therapeutics''. 1958 Nov;124(3):260-3. PMID 13588540</ref> but is a useful intermediate which can be used to produce both ]s such as ], and also potent opioid agonists such as ].<ref>Daniel Lednicer. Central Analgetics. (1982), p146. ISBN 0-471-08314-3 </ref> It is also produced as a major metabolite of morphine,<ref>Yeh SY. Urinary excretion of morphine and its metabolites in morphine-dependent subjects. ''Journal of Pharmacology and Experimental Therapeutics''. 1975 Jan;192(1):201-10. PMID 235634</ref> with its formation from morphine catalysed by the liver enzymes CYP3A4 and CYP2C8.<ref>Projean D, Morin PE, Tu TM, Ducharme J. Identification of CYP3A4 and CYP2C8 as the major cytochrome P450 s responsible for morphine N-demethylation in human liver microsomes. ''Xenobiotica''. 2003 Aug;33(8):841-54. PMID 12936704</ref>


== References == == References ==
{{reflist}} {{Reflist}}


{{Opioidergics}}

⚫ ]
] ]
] ]
] ]
⚫ ]
] ]

]
]

Latest revision as of 18:04, 21 October 2024

Chemical compound Pharmaceutical compound
Normorphine
Clinical data
Other namesNormorphine
Dependence
liability		High
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • 3,6α-Dihydroxy-4,5α-epoxy-7,8-didehydromorphinan
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.712 Edit this at Wikidata
Chemical and physical data
FormulaC16H17NO3
Molar mass271.316 g·mol
3D model (JSmol)
SMILES
  • c1cc(c2c3c1C453(CCN4)(O2)(C=C5)O)O
InChI
  • InChI=1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2/t9-,10+,12-,15-,16-/m0/s1
  • Key:ONBWJWYUHXVEJS-ZTYRTETDSA-N
  (what is this?)  (verify)

Normorphine is an opiate analogue, the N-demethylated derivative of morphine, that was first described in the 1950s when a large group of N-substituted morphine analogues were characterized for activity. The compound has relatively little opioid activity in its own right, but is a useful intermediate which can be used to produce both opioid antagonists such as nalorphine, and also potent opioid agonists such as N-phenethylnormorphine. with its formation from morphine catalyzed by the liver enzymes CYP3A4 and CYP2C8.

Normorphine is a controlled substance listed under the Single Convention On Narcotic Drugs 1961 and the laws in various states implementing it; for example, in the United States it is a Schedule I Narcotic controlled substance, with an ACSCN of 9313 and an annual aggregate manufacturing quota of 18 grams in 2014, unchanged from the prior year. The salts in use are the free base hexahydrate (free base conversion ratio 0.715), and hydrochloride (0.833).

References

  1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. Clark RL, Pessolano AA, Weijlard J, Pfister K (October 1953). "N-Substituted epoxymorphinans". Journal of the American Chemical Society. 75 (20): 4963–7. doi:10.1021/ja01116a024.
  3. Fraser HF, Wikler A, Van Horn GD, Eisenman AJ, Isbell H (March 1958). "Human pharmacology and addiction liability of normorphine". The Journal of Pharmacology and Experimental Therapeutics. 122 (3): 359–69. PMID 13539761.
  4. Lasagna L, De Kornfeld TJ (November 1958). "Analgesic potency of normorphine in patients with postoperative pain". The Journal of Pharmacology and Experimental Therapeutics. 124 (3): 260–3. PMID 13588540.
  5. Yeh SY (January 1975). "Urinary excretion of morphine and its metabolites in morphine-dependent subjects". The Journal of Pharmacology and Experimental Therapeutics. 192 (1): 201–10. PMID 235634.
  6. Projean D, Morin PE, Tu TM, Ducharme J (August 2003). "Identification of CYP3A4 and CYP2C8 as the major cytochrome P450 s responsible for morphine N-demethylation in human liver microsomes". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 33 (8): 841–54. doi:10.1080/0049825031000121608. PMID 12936704. S2CID 41467595.
  7. "Quotas - 2014". DEA Diversion Control Division.
Opioid receptor modulators
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
  • Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
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