| Revision as of 14:10, 3 September 2011 editBogBot (talk | contribs)Bots53,132 edits populated new fields in {{drugbox}} and reordered per bot approval. Report errors and suggestions to User_talk:BogBot← Previous edit |
Latest revision as of 02:46, 26 January 2024 edit undoVipsmat (talk | contribs)177 editsm formatting |
| (37 intermediate revisions by 20 users not shown) |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| Watchedfields = changed |
|
| verifiedrevid = 407706655 |
|
| verifiedrevid = 448227671 |
|
| IUPAC_name = ''cis''-5-hydroxy-1-methyl-2-(''N'',''N''-propylamino)tetralin |
|
| IUPAC_name = (1''S'',2''R'')-5-Methoxy-1-methyl-2-(''N'',''N''-propylamino)tetralin |
|
| image = UH-232_structure.png |
|
| image = UH-232 Structure.svg |
|
|
|
|
|
<!--Clinical data--> |
|
<!--Clinical data--> |
| Line 8: |
Line 10: |
|
| pregnancy_category = |
|
| pregnancy_category = |
|
| legal_status = |
|
| legal_status = |
|
| routes_of_administration = |
|
| routes_of_administration = |
|
|
|
|
|
<!--Pharmacokinetic data--> |
|
<!--Pharmacokinetic data--> |
| Line 14: |
Line 16: |
|
| metabolism = |
|
| metabolism = |
|
| elimination_half-life = |
|
| elimination_half-life = |
|
| excretion = |
|
| excretion = |
|
|
|
|
|
<!--Identifiers--> |
|
<!--Identifiers--> |
|
|
| CAS_number_Ref = {{cascite|correct|??}} |
|
| CAS_number = 95999-12-5 |
|
| CAS_number = 95999-12-5 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = QQYOR9S587 |
|
| ATC_prefix = none |
|
| ATC_prefix = none |
|
| ATC_suffix = |
|
| ATC_suffix = |
| Line 24: |
Line 29: |
|
<!--Chemical data--> |
|
<!--Chemical data--> |
|
| C=18 | H=29 | N=1 | O=1 |
|
| C=18 | H=29 | N=1 | O=1 |
|
| molecular_weight = 275.428 g/mol |
|
|
| smiles = CC2C(N(CCC)CCC)CCc1c2cccc1OC |
|
| smiles = CC2C(N(CCC)CCC)CCc1c2cccc1OC |
|
}} |
|
}} |
|
|
|
|
|
'''UH-232''' ('''(+)-UH232''') is a drug which acts as a subtype selective mixed agonist-antagonist for ]s, acting as a weak ] at the ] subtype,<ref>{{cite journal | last1 = Griffon | first1 = N | last2 = Pilon | first2 = C | last3 = Schwartz | first3 = JC | last4 = Sokoloff | first4 = P | title = The preferential dopamine D3 receptor ligand, (+)-UH232, is a partial agonist | journal = European journal of pharmacology | volume = 282 | issue = 1-3 | pages = R3–4 | year = 1995 | pmid = 7498261 }}</ref> and an antagonist at D<sub>2</sub>Sh ]s on dopaminergic nerve terminals.<ref>{{cite journal | last1 = Waters | first1 = N | last2 = Lagerkvist | first2 = S | last3 = Löfberg | first3 = L | last4 = Piercey | first4 = M | last5 = Carlsson | first5 = A | title = The dopamine D3 receptor and autoreceptor preferring antagonists (+)-AJ76 and (+)-UH232; a microdialysis study | journal = European journal of pharmacology | volume = 242 | issue = 2 | pages = 151–63 | year = 1993 | pmid = 8253112 }}</ref><ref>{{cite journal | last1 = Aretha | first1 = CW | last2 = Sinha | first2 = A | last3 = Galloway | first3 = MP | title = Dopamine D3-preferring ligands act at synthesis modulating autoreceptors | journal = The Journal of pharmacology and experimental therapeutics | volume = 274 | issue = 2 | pages = 609–13 | year = 1995 | pmid = 7636720 }}</ref> This causes dopamine release in the brain and has a ] effect,<ref>{{cite journal | last1 = Waters | first1 = N | last2 = Hansson | first2 = L | last3 = Löfberg | first3 = L | last4 = Carlsson | first4 = A | title = Intracerebral infusion of (+)-AJ76 and (+)-UH232: effects on dopamine release and metabolism in vivo | journal = European journal of pharmacology | volume = 251 | issue = 2-3 | pages = 181–90 | year = 1994 | pmid = 8149975 }}</ref><ref>{{cite journal | last1 = Sotnikova | first1 = TD | last2 = Gainetdinov | first2 = RR | last3 = Grekhova | first3 = TV | last4 = Rayevsky | first4 = KS | title = Effects of intrastriatal infusion of D2 and D3 dopamine receptor preferring antagonists on dopamine release in rat dorsal striatum (in vivo microdialysis study) | journal = Pharmacological research : the official journal of the Italian Pharmacological Society | volume = 43 | issue = 3 | pages = 283–90 | year = 2001 | pmid = 11401421 | doi = 10.1006/phrs.2000.0773 }}</ref><ref>{{cite journal | last1 = Millan | first1 = MJ | last2 = Seguin | first2 = L | last3 = Gobert | first3 = A | last4 = Cussac | first4 = D | last5 = Brocco | first5 = M | title = The role of dopamine D3 compared with D2 receptors in the control of locomotor activity: a combined behavioural and neurochemical analysis with novel, selective antagonists in rats | journal = Psychopharmacology | volume = 174 | issue = 3 | pages = 341–57 | year = 2004 | pmid = 14985929 | doi = 10.1007/s00213-003-1770-x }}</ref> as well as blocking the behavioural effects of cocaine.<ref>{{cite journal | last1 = Piercey | first1 = MF | last2 = Lum | first2 = JT | last3 = Hoffmann | first3 = WE | last4 = Carlsson | first4 = A | last5 = Ljung | first5 = E | last6 = Svensson | first6 = K | title = Antagonism of cocaine's pharmacological effects by the stimulant dopaminergic antagonists, (+)-AJ76 and (+)-UH232 | journal = Brain research | volume = 588 | issue = 2 | pages = 217–22 | year = 1992 | pmid = 1393576 | doi=10.1016/0006-8993(92)91578-3}}</ref> It was trialled for the treatment of schizophrenia but unexpectedly caused symptoms to become worse.<ref>{{cite journal | last1 = Lahti | first1 = AC | last2 = Weiler | first2 = M | last3 = Carlsson | first3 = A | last4 = Tamminga | first4 = CA | title = Effects of the D3 and autoreceptor-preferring dopamine antagonist (+)-UH232 in schizophrenia | journal = Journal of neural transmission (Vienna, Austria : 1996) | volume = 105 | issue = 6-7 | pages = 719–34 | year = 1998 | pmid = 9826114 }}</ref> |
|
'''UH-232''' ('''(+)-UH232''') is a drug which acts as a subtype selective mixed agonist-antagonist for ]s, acting as a weak ] at the ] subtype,<ref>{{cite journal | vauthors = Griffon N, Pilon C, Schwartz JC, Sokoloff P | title = The preferential dopamine D3 receptor ligand, (+)-UH232, is a partial agonist | journal = European Journal of Pharmacology | volume = 282 | issue = 1–3 | pages = R3-4 | date = August 1995 | pmid = 7498261 | doi = 10.1016/0014-2999(95)00460-3 }}</ref> and an antagonist at D<sub>2</sub>Sh ]s on dopaminergic nerve terminals.<ref>{{cite journal | vauthors = Svensson K, Johansson AM, Magnusson T, Carlsson A | title = (+)-AJ 76 and (+)-UH 232: central stimulants acting as preferential dopamine autoreceptor antagonists | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 334 | issue = 3 | pages = 234–45 | date = November 1986 | pmid = 2880302| doi = 10.1007/BF00508777 | s2cid = 6686333 }}</ref><ref>{{cite journal | vauthors = Waters N, Lagerkvist S, Löfberg L, Piercey M, Carlsson A | title = The dopamine D3 receptor and autoreceptor preferring antagonists (+)-AJ76 and (+)-UH232; a microdialysis study | journal = European Journal of Pharmacology | volume = 242 | issue = 2 | pages = 151–63 | date = September 1993 | pmid = 8253112 | doi = 10.1016/0014-2999(93)90075-S }}</ref><ref>{{cite journal | vauthors = Aretha CW, Sinha A, Galloway MP | title = Dopamine D3-preferring ligands act at synthesis modulating autoreceptors | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 274 | issue = 2 | pages = 609–13 | date = August 1995 | pmid = 7636720 }}</ref> It causes dopamine release in the brain and has a ] effect,<ref>{{cite journal | vauthors = Waters N, Hansson L, Löfberg L, Carlsson A | title = Intracerebral infusion of (+)-AJ76 and (+)-UH232: effects on dopamine release and metabolism in vivo | journal = European Journal of Pharmacology | volume = 251 | issue = 2–3 | pages = 181–90 | date = January 1994 | pmid = 8149975 | doi = 10.1016/0014-2999(94)90399-9 }}</ref><ref>{{cite journal | vauthors = Sotnikova TD, Gainetdinov RR, Grekhova TV, Rayevsky KS | title = Effects of intrastriatal infusion of D2 and D3 dopamine receptor preferring antagonists on dopamine release in rat dorsal striatum (in vivo microdialysis study) | journal = Pharmacological Research | volume = 43 | issue = 3 | pages = 283–90 | date = March 2001 | pmid = 11401421 | doi = 10.1006/phrs.2000.0773 }}</ref><ref>{{cite journal | vauthors = Millan MJ, Seguin L, Gobert A, Cussac D, Brocco M | title = The role of dopamine D3 compared with D2 receptors in the control of locomotor activity: a combined behavioural and neurochemical analysis with novel, selective antagonists in rats | journal = Psychopharmacology | volume = 174 | issue = 3 | pages = 341–57 | date = July 2004 | pmid = 14985929 | doi = 10.1007/s00213-003-1770-x | s2cid = 1592299 }}</ref> as well as blocking the behavioural effects of cocaine.<ref>{{cite journal | vauthors = Piercey MF, Lum JT, Hoffmann WE, Carlsson A, Ljung E, Svensson K | title = Antagonism of cocaine's pharmacological effects by the stimulant dopaminergic antagonists, (+)-AJ76 and (+)-UH232 | journal = Brain Research | volume = 588 | issue = 2 | pages = 217–22 | date = August 1992 | pmid = 1393576 | doi = 10.1016/0006-8993(92)91578-3 | s2cid = 44478271 }}</ref> It may also serve as a ] agonist, based on animal studies.<ref name="schiz">{{cite journal | vauthors = Lahti AC, Weiler M, Carlsson A, Tamminga CA | title = Effects of the D3 and autoreceptor-preferring dopamine antagonist (+)-UH232 in schizophrenia | journal = Journal of Neural Transmission | volume = 105 | issue = 6–7 | pages = 719–34 | year = 1998 | pmid = 9826114 | doi = 10.1007/s007020050091 | s2cid = 31976950 }}</ref> |
|
|
It was investigated in clinical trials for the treatment of schizophrenia, but unexpectedly caused symptoms to become worse.<ref name="schiz"/> |
|
|
|
|
|
==(+)-AJ76== |
|
|
The N-monopropyl derivative (+)-AJ76 is an active metabolite of UH-232 and has practically identical effects. |
|
|
]] |
|
|
{{clear-left}} |
|
|
|
|
|
== See also == |
|
== See also == |
|
* ] |
|
* ] |
|
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
|
* ] |
|
|
|
|
|
== References == |
|
== References == |
|
{{Reflist|4}} |
|
{{Reflist}} |
|
|
|
|
|
{{Dopaminergics}} |
|
{{Dopaminergics}} |
|
|
|
|
|
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |