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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 448227671
| verifiedrevid = 448227671
| IUPAC_name = (1S,2R)-5-methoxy-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-->
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| pregnancy_category =
| pregnancy_category =
| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
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| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| 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 =
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<!--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 [[dopamine receptor]]s, acting as a weak [[partial agonist]] at the [[Dopamine receptor D3|D<sub>3</sub>]] 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 | doi=10.1016/0014-2999(95)00460-3}}</ref> and an antagonist at D<sub>2</sub>Sh [[autoreceptor]]s on dopaminergic nerve terminals.<ref>{{Cite doi|10.1007/BF00508777}}</ref><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 | doi=10.1016/0014-2999(93)90075-S}}</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 [[stimulant]] 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 | doi=10.1016/0014-2999(94)90399-9}}</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 | doi = 10.1007/s007020050091 }}</ref>
'''UH-232''' ('''(+)-UH232''') is a drug which acts as a subtype selective mixed agonist-antagonist for [[dopamine receptor]]s, acting as a weak [[partial agonist]] at the [[Dopamine receptor D3|D<sub>3</sub>]] 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 [[autoreceptor]]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 [[stimulant]] 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 [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] 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.
[[Image:(+)-AJ76_structure.png|200px|thumb|left|(+)-AJ76, CAS# 85378-82-1, [https://pubchem.ncbi.nlm.nih.gov/compound/13755572 13755572]]]
{{clear-left}}


== See also ==
== See also ==
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{{Dopaminergics}}
{{Dopaminergics}}


⚫
[[Category:2-Aminotetralins]]
[[Category:Stimulants]]
[[Category:Stimulants]]
[[Category:Phenol ethers]]
[[Category:Phenol ethers]]
⚫
[[Category:Tetralins]]
[[Category:Amines]]
[[Category:Dopamine antagonists]]
[[Category:Dopamine antagonists]]
[[Category:Dopamine agonists]]
[[Category:Dopamine agonists]]

Latest revision as of 02:46, 26 January 2024

UH-232
Clinical data
ATC code
  • none
Identifiers
  • (1S,2R)-5-Methoxy-1-methyl-2-(N,N-propylamino)tetralin
CAS Number
PubChem CID
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H29NO
Molar mass275.436 g·mol−1
3D model (JSmol)
  • CC2C(N(CCC)CCC)CCc1c2cccc1OC
  (verify)

UH-232 ((+)-UH232) is a drug which acts as a subtype selective mixed agonist-antagonist for dopamine receptors, acting as a weak partial agonist at the D3 subtype,[1] and an antagonist at D2Sh autoreceptors on dopaminergic nerve terminals.[2][3][4] It causes dopamine release in the brain and has a stimulant effect,[5][6][7] as well as blocking the behavioural effects of cocaine.[8] It may also serve as a 5-HT2A receptor agonist, based on animal studies.[9] It was investigated in clinical trials for the treatment of schizophrenia, but unexpectedly caused symptoms to become worse.[9]

(+)-AJ76

[edit]

The N-monopropyl derivative (+)-AJ76 is an active metabolite of UH-232 and has practically identical effects.

(+)-AJ76, CAS# 85378-82-1, 13755572

See also

[edit]

References

[edit]
  1. ^ Griffon N, Pilon C, Schwartz JC, Sokoloff P (August 1995). "The preferential dopamine D3 receptor ligand, (+)-UH232, is a partial agonist". European Journal of Pharmacology. 282 (1–3): R3-4. doi:10.1016/0014-2999(95)00460-3. PMID 7498261.
  2. ^ Svensson K, Johansson AM, Magnusson T, Carlsson A (November 1986). "(+)-AJ 76 and (+)-UH 232: central stimulants acting as preferential dopamine autoreceptor antagonists". Naunyn-Schmiedeberg's Archives of Pharmacology. 334 (3): 234–45. doi:10.1007/BF00508777. PMID 2880302. S2CID 6686333.
  3. ^ Waters N, Lagerkvist S, Löfberg L, Piercey M, Carlsson A (September 1993). "The dopamine D3 receptor and autoreceptor preferring antagonists (+)-AJ76 and (+)-UH232; a microdialysis study". European Journal of Pharmacology. 242 (2): 151–63. doi:10.1016/0014-2999(93)90075-S. PMID 8253112.
  4. ^ Aretha CW, Sinha A, Galloway MP (August 1995). "Dopamine D3-preferring ligands act at synthesis modulating autoreceptors". The Journal of Pharmacology and Experimental Therapeutics. 274 (2): 609–13. PMID 7636720.
  5. ^ Waters N, Hansson L, Löfberg L, Carlsson A (January 1994). "Intracerebral infusion of (+)-AJ76 and (+)-UH232: effects on dopamine release and metabolism in vivo". European Journal of Pharmacology. 251 (2–3): 181–90. doi:10.1016/0014-2999(94)90399-9. PMID 8149975.
  6. ^ Sotnikova TD, Gainetdinov RR, Grekhova TV, Rayevsky KS (March 2001). "Effects of intrastriatal infusion of D2 and D3 dopamine receptor preferring antagonists on dopamine release in rat dorsal striatum (in vivo microdialysis study)". Pharmacological Research. 43 (3): 283–90. doi:10.1006/phrs.2000.0773. PMID 11401421.
  7. ^ Millan MJ, Seguin L, Gobert A, Cussac D, Brocco M (July 2004). "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". Psychopharmacology. 174 (3): 341–57. doi:10.1007/s00213-003-1770-x. PMID 14985929. S2CID 1592299.
  8. ^ Piercey MF, Lum JT, Hoffmann WE, Carlsson A, Ljung E, Svensson K (August 1992). "Antagonism of cocaine's pharmacological effects by the stimulant dopaminergic antagonists, (+)-AJ76 and (+)-UH232". Brain Research. 588 (2): 217–22. doi:10.1016/0006-8993(92)91578-3. PMID 1393576. S2CID 44478271.
  9. ^ a b Lahti AC, Weiler M, Carlsson A, Tamminga CA (1998). "Effects of the D3 and autoreceptor-preferring dopamine antagonist (+)-UH232 in schizophrenia". Journal of Neural Transmission. 105 (6–7): 719–34. doi:10.1007/s007020050091. PMID 9826114. S2CID 31976950.
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