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{{Short description|Racemic mixture}}
{{Distinguish|racemethorphan|morphan}}
{{Distinguish|racemethorphan|morphan}}
{{Drugbox
{{Drugbox
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| pregnancy_category =
| pregnancy_category =
| legal_AU = S9
| legal_AU = S9
| legal_BR = A1
| 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=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = Schedule I
| legal_CA = Schedule I
| legal_DE = Anlage II
| legal_DE = Anlage II
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<!--Chemical data-->
<!--Chemical data-->
| C=17 | H=23 | N=1 | O=1
| C=17 | H=23 | N=1 | O=1
| molecular_weight = 257.37 g/mol
| StdInChI = 1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3
| StdInChI = 1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3
| StdInChIKey = JAQUASYNZVUNQP-UHFFFAOYSA-N
| StdInChIKey = JAQUASYNZVUNQP-UHFFFAOYSA-N
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'''Racemorphan''', or '''morphanol''', is the [[racemic mixture]] of the two [[stereoisomer]]s of 17-methylmorphinan-3-ol, each with differing [[pharmacology]] and [[therapeutic effect|effect]]s:
'''Racemorphan''', or '''morphanol''', is the [[racemic mixture]] of the two [[stereoisomer]]s of 17-methylmorphinan-3-ol, each with differing [[pharmacology]] and [[therapeutic effect|effect]]s:


* [[Dextrorphan]] - an [[antitussive]] and [[dissociative drug|dissociative]] [[hallucinogen]] ([[NMDA receptor antagonist]])
* [[Dextrorphan]]{{snd}} an [[antitussive]] and [[dissociative drug|dissociative]] [[hallucinogen]] ([[NMDA receptor antagonist]])
* [[Levorphanol]] - an [[opioid]] [[analgesic]]
* [[Levorphanol]]{{snd}} an [[opioid]] [[analgesic]]


Racemorphan itself is under international control per the Single Convention on Narcotic Drugs 1961 and is therefore listed as a Schedule II Narcotic controlled substance in the US Controlled Substances Act 1970; it has an ACSCN of 9733 and in 2014 it had an aggregate annual manufacturing quota of zero. <ref>http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html</ref> The salts in use are hydrobromide (free base conversion ratio 0.741), hydrochloride (0.876), and tartrate (0.632).
Racemorphan itself is under international control per the Single Convention on Narcotic Drugs 1961 and is therefore listed as a Schedule II Narcotic controlled substance in the US Controlled Substances Act 1970; it has an ACSCN of 9733 and in 2014 it had an aggregate annual manufacturing quota of zero. <ref>{{cite web|url=http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html|title=Conversion Factors for Controlled Substances|website=www.deadiversion.usdoj.gov}}</ref> The salts in use are hydrobromide (free base conversion ratio 0.741), hydrochloride (0.876), and tartrate (0.632).


==See also==
==See also==
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* [[Morphinan]]
* [[Morphinan]]
* [[Cyclorphan]]
* [[Cyclorphan]]

== See also ==
* [[Cough syrup]]
* [[Noscapine]]
* [[Codeine]]; [[Pholcodine]]
* [[Dextromethorphan]]; [[Dimemorfan]]
* [[Dextrorphan]]; [[Levorphanol]]
* [[Butamirate]]
* [[Pentoxyverine]]
* [[Tipepidine]]
* [[Cloperastine]]
* [[Levocloperastine]]


==References==
==References==
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[[Category:NMDA receptor antagonists]]
[[Category:NMDA receptor antagonists]]
[[Category:Nicotinic antagonists]]
[[Category:Nicotinic antagonists]]
[[Category:Mu-opioid agonists]]
[[Category:Mu-opioid receptor agonists]]
[[Category:Serotonin-norepinephrine reuptake inhibitors]]
[[Category:Serotonin–norepinephrine reuptake inhibitors]]
[[Category:Sigma agonists]]
[[Category:Sigma agonists]]
[[Category:Calcium channel blockers]]
[[Category:Calcium channel blockers]]
[[Category:Dissociative drugs]]





Revision as of 00:30, 26 March 2024

Racemorphan
Legal status
Legal status
Identifiers
  • (±)-17-Methylmorphinan-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard100.005.499 Edit this at Wikidata
Chemical and physical data
FormulaC17H23NO
Molar mass257.377 g·mol−1
3D model (JSmol)
  • CN1CCC23CCCCC2C1Cc4ccc(O)cc34
  • InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3
  • Key:JAQUASYNZVUNQP-UHFFFAOYSA-N

Racemorphan, or morphanol, is the racemic mixture of the two stereoisomers of 17-methylmorphinan-3-ol, each with differing pharmacology and effects:

Racemorphan itself is under international control per the Single Convention on Narcotic Drugs 1961 and is therefore listed as a Schedule II Narcotic controlled substance in the US Controlled Substances Act 1970; it has an ACSCN of 9733 and in 2014 it had an aggregate annual manufacturing quota of zero. [2] The salts in use are hydrobromide (free base conversion ratio 0.741), hydrochloride (0.876), and tartrate (0.632).

See also

See also

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. ^ "Conversion Factors for Controlled Substances". www.deadiversion.usdoj.gov.