Acetyldihydrocodeine: Difference between revisions

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Acetyldihydrocodeine
Clinical data
Synonyms	Acetyldihydrocodeine, Dihydrothebacone, 6-acetyl-7,8-dihydrocodeine
AHFS/Drugs.com	International Drug Names
ATC code	R05DA12 (WHO) ;
Legal status
Legal status	US: Schedule I ;
Identifiers
	IUPAC name 3-methoxy-6-acetoxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan;
CAS Number	3861-72-1 ;
PubChem CID	5463874;
DrugBank	DB01538 ;
ChemSpider	4576412 ;
UNII	SGY1T84P34;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C20H25NO4
Molar mass	343.417 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C(O[C@@H]4[C@@H]5Oc1c2c(ccc1OC)C[C@H]3N(CC[C@]25[C@H]3CC4)C)C;
	InChI InChI=1S/C20H25NO4/c1-11(22)24-16-7-5-13-14-10-12-4-6-15(23-3)18-17(12)20(13,19(16)25-18)8-9-21(14)2/h4,6,13-14,16,19H,5,7-10H2,1-3H3/t13-,14+,16-,19-,20-/m0/s1 ; Key:LGGDXXJAGWBUSL-BKRJIHRRSA-N ;
(what is this?) (verify)

VisualWikitext

Latest revision as of 17:22, 9 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Acetyldihydrocodeine is an opiate derivative discovered in Germany in 1914^[1] and was used as a cough suppressant and analgesic. It is not commonly used, but has activity similar to other opiates. Acetyldihydrocodeine is a very close relative derivative of Thebacon, where only the 6-7 double bond is unsaturated. Acetyldihydrocodeine can be described as the 6-acetyl derivative of dihydrocodeine and is metabolised in the liver by demethylation and deacetylation to produce dihydromorphine.

Since acetyldihydrocodeine has higher lipophilicity than codeine and is converted into dihydromorphine rather than morphine, it can be expected to be more potent and longer lasting, and also have higher bioavailability than codeine. Side effects are similar to those of other opiates and include itching, nausea and respiratory depression.

Although an opioid of low to moderate strength and use in medicine elsewhere in the world, acetyldihydrocodeine is a Schedule I controlled substance in the United States. Its DEA Administrative Controlled Substances Control Number is 9051 and the one salt in use, acetyldihydrocodeine hydrochloride, has a freebase conversion ratio of 0.90. The 2013 annual production quota from the DEA is 2 grammes.

References

↑ v. Braun, J. (1914). "Untersuchungen über Morphium-Alkaloide". Chemische Berichte. 47 (2): 2312–2330. doi:10.1002/cber.191404702149.

Template:Cough and cold preparations

[1] v. Braun, J. (1914). "Untersuchungen über Morphium-Alkaloide". Chemische Berichte. 47 (2): 2312–2330. doi:10.1002/cber.191404702149.

[1]

@@ Line 1: / Line 1: @@
-{{drugbox |
+{{Drugbox
-| IUPAC_name        = 3-methoxy-6-acetoxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan
+| Verifiedfields = changed
-| image             = Acetyldihydrocodeine.svg
+| Watchedfields = changed
-| width             = 200
+| verifiedrevid = 477240369
-| CAS_number        = 3861-72-1
+| IUPAC_name = 3-methoxy-6-acetoxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan
-| synonyms  = Acetyldihydrocodeine, Dihydrothebacone, 6-acetyl-7,8-dihydrocodeine
+| image = Acetyldihydrocodeine.png
-| ATC_prefix        = R05
+| width = 200
-| ATC_suffix        = DA12
+| image2 = Acetyldihydrocodeine0.png
-| PubChem           = 5463874
-| DrugBank          =
+<!--Clinical data-->
-| C = 20 | H = 25 | N = 1 | O = 4
+| tradename =
-| molecular_weight  = 343.417 g/mol
+| Drugs.com = {{drugs.com|international|acetyldihydrocodeine}}
-| bioavailability   =
+| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
-| protein_bound     =
+| pregnancy_US = <!-- A / B / C / D / X -->
-| metabolism        =
+| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
-| elimination_half-life =
+| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
-| excretion         =
+| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
-| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
+| legal_US = Schedule I
-| pregnancy_US      =  <!-- A / B            / C / D / X -->
-| pregnancy_category=
+<!--Identifiers-->
-| legal_AU          =  <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
+| CAS_number_Ref = {{cascite|changed|??}}
-| legal_CA          =  <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
+| CAS_number = 3861-72-1
-| legal_UK          =  <!-- GSL         / P       / POM / CD / Class A, B, C -->
+| ATC_prefix = R05
-| legal_US          =  <!-- ?Schedule II -->
+| ATC_suffix = DA12
-| legal_status      =
+| PubChem = 5463874
-| routes_of_administration =
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| DrugBank = DB01538
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 4576412
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = SGY1T84P34
+<!--Chemical data-->
+| C=20 | H=25 | N=1 | O=4
+| molecular_weight = 343.417 g/mol
+| smiles = O=C(O[C@@H]4[C@@H]5Oc1c2c(ccc1OC)C[C@H]3N(CC[C@]25[C@H]3CC4)C)C
+| InChI = 1/C20H25NO4/c1-11(22)24-16-7-5-13-14-10-12-4-6-15(23-3)18-17(12)20(13,19(16)25-18)8-9-21(14)2/h4,6,13-14,16,19H,5,7-10H2,1-3H3/t13-,14+,16-,19-,20-/m0/s1
+| InChIKey = LGGDXXJAGWBUSL-BKRJIHRRBN
+| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChI = 1S/C20H25NO4/c1-11(22)24-16-7-5-13-14-10-12-4-6-15(23-3)18-17(12)20(13,19(16)25-18)8-9-21(14)2/h4,6,13-14,16,19H,5,7-10H2,1-3H3/t13-,14+,16-,19-,20-/m0/s1
+| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChIKey = LGGDXXJAGWBUSL-BKRJIHRRSA-N
+| synonyms = Acetyldihydrocodeine, Dihydrothebacone, 6-acetyl-7,8-dihydrocodeine
 }}
+__NOTOC__
+{{SI}}
+{{CMG}}
+==Overview==
+'''Acetyldihydrocodeine''' is an [[opiate]] derivative discovered in Germany in 1914<ref>{{cite journal|author = v. Braun, J.|title = Untersuchungen über Morphium-Alkaloide|journal = Chemische Berichte|year = 1914|volume = 47|issue = 2|pages = 2312–2330|doi = 10.1002/cber.191404702149}}</ref> and was used  as a cough suppressant and [[analgesic]]. It is not commonly used, but has activity similar to other opiates. Acetyldihydrocodeine is a very close relative derivative of [[Thebacon]], where only the 6-7 [[double bond]] is unsaturated. Acetyldihydrocodeine can be described as the 6-acetyl derivative of [[dihydrocodeine]] and is metabolised in the liver by demethylation and deacetylation to produce [[dihydromorphine]].
-'''Acetyldihydrocodeine''' is an [[opiate]] derivative developed as a cough suppressant and [[analgesic]]. It is not commonly used, but has activity similar to other opiates. Acetyldihydrocodeine can be described as the 6-acetyl derivative of [[dihydrocodeine]] and is metabolised in the liver by demethylation and deacetylation to produce [[dihydromorphine]].
+Since acetyldihydrocodeine has higher [[lipophilicity]] than [[codeine]] and is converted into dihydromorphine rather than [[morphine]], it can be expected to be more potent and longer lasting, and also have higher [[bioavailability]] than codeine. Side effects are similar to those of other [[opiates]] and include [[itching]], [[nausea]] and [[respiratory depression]].
-Since acetyldihydrocodeine has higher lipophilicity than [[codeine]] and is converted into dihydromorphine rather than [[morphine]], it can be expected to be more potent and longer lasting, and also have higher [[bioavailability]] than codeine. Side effects are similar to those of other [[opiates]] and include [[itching]], [[nausea]] and [[respiratory depression]].
+Although an opioid of low to moderate strength and use in medicine elsewhere in the world, acetyldihydrocodeine is a Schedule I controlled substance in the United States. Its DEA Administrative Controlled Substances Control Number is 9051 and the one salt in use, acetyldihydrocodeine hydrochloride, has a freebase conversion ratio of 0.90.  The 2013 annual production quota from the DEA is 2 grammes.
+== References ==
+{{Reflist|2}}
-{{opioids}}
 {{Cough and cold preparations}}
-[[Category:Drugs]]
+[[Category:Analgesics]]
-{{WikiDoc Help Menu}}
+[[Category:Morphinans]]
-{{WikiDoc Sources}}
+[[Category:Phenol ethers]]
+[[Category:Mu-opioid agonists]]
+[[Category:Semisynthetic_opioids]]
+[[Category:Drug]]

Acetyldihydrocodeine: Difference between revisions

Latest revision as of 17:22, 9 April 2015

Overview

References

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