1-(2-Bromo-4,5-dimethoxybenzyl)-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline Solid powder Others A 69024 is a highly selective dopamine D-1 receptor antagonist. It is a radioligand that may antagonize self-mutilatory behavior. 422.3 g/mol
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Formulation: 422.3 g/mol
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1-(2-Bromo-4,5-dimethoxybenzyl)-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline - 58939-37-0

1-(2-Bromo-4,5-dimethoxybenzyl)-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

The product is for non-human research only. Not for therapeutic or veterinary use.

Catalog Number: BT-257855

CAS Number: 58939-37-0

Molecular Formula: C20H24BrNO4

Molecular Weight: 422.3 g/mol

CAS Number 58939-37-0
Product Name 1-(2-Bromo-4,5-dimethoxybenzyl)-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
Molecular Formula C20H24BrNO4
Molecular Weight 422.3 g/mol
Appearance Solid powder
InChI InChI=1S/C20H24BrNO4/c1-22-6-5-12-8-18(24-2)17(23)10-14(12)16(22)7-13-9-19(25-3)20(26-4)11-15(13)21/h8-11,16,23H,5-7H2,1-4H3
InChI Key YVBUTIYRCMQJHW-UHFFFAOYSA-N
IUPAC Name 1-[(2-bromo-4,5-dimethoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
Canonical SMILES CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3Br)OC)OC)O)OC
Description A 69024 is a highly selective dopamine D-1 receptor antagonist. It is a radioligand that may antagonize self-mutilatory behavior.
Shelf Life >2 years if stored properly
SMILES CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3Br)OC)OC)O)OC
Solubility Soluble in DMSO
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Synonyms 1-(2-bromo-4,5-dimethoxybenzyl)-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
A 66359
A 69024
A-66359
A-69024
Reference 1: Kassiou M, Loc'h C, Bottlaender M, Mardon K, Ottaviani M, Coulon C, Katsifis A, Maziere B. (+)-[76Br]A-69024: a non-benzazepine radioligand for studies of dopamine D1 receptors using PET. Nucl Med Biol. 2002 Apr;29(3):295-302. PubMed PMID: 11929698. 2: Kassiou M, Mardon K, Mattner F, Katsifis A, Dikic B. Pharmacological evaluation of (+)-2- [123I]A-69024: a radioligand for in vivo studies of dopamine D1 receptors. Life Sci. 2001 Jun 29;69(6):669-75. PubMed PMID: 11476188. 3: Kerkman DJ, Ackerman M, Artman LD, MacKenzie RG, Johnson MC, Bednarz L, Montana W, Asin KE, Stampfli H, Kebabian JW. A-69024: a non-benzazepine antagonist with selectivity for the dopamine D-1 receptor. Eur J Pharmacol. 1989 Aug 3;166(3):481-91. PubMed PMID: 2509217. 4: Criswell HE, Mueller RA, Breese GR. Pharmacologic evaluation of SCH-39166, A-69024, NO-0756, and SCH-23390 in neonatal-6-OHDA-lesioned rats. Further evidence that self-mutilatory behavior induced by L-dopa is related to D1 dopamine receptors. Neuropsychopharmacology. 1992 Sep;7(2):95-103. PubMed PMID: 1418306. 5: Kassiou M, Scheffel U, Ravert HT, Mathews WB, Musachio JL, Lambrecht RM, Dannals RF. [11C]A-69024: a potent and selective non-benzazepine radiotracer for in vivo studies of dopamine D1 receptors. Nucl Med Biol. 1995 Feb;22(2):221-6. PubMed PMID: 7767316. 6: Besret L, Dollé F, Hérard AS, Guillermier M, Demphel S, Hinnen F, Coulon C, Ottaviani M, Bottlaender M, Hantraye P, Kassiou M. Dopamine D1 receptor imaging in the rodent and primate brain using the isoquinoline +-[11C]A-69024 and positron emission tomography. J Pharm Sci. 2008 Jul;97(7):2811-9. PubMed PMID: 17786986. 7: Kassiou M, Scheffel UA, Musachio JL, Stathis M, Dannals RF. [3H]A-69024: a non-benzazepine ligand for in vitro and in vivo studies of dopamine D1 receptors. Life Sci. 1995;57(23):PL367-72. PubMed PMID: 7475960. 8: Daly SA, Waddington JL. Two directions of dopamine D1/D2 receptor interaction in studies of behavioural regulation: a finding generic to four new, selective dopamine D1 receptor antagonists. Eur J Pharmacol. 1992 Mar 24;213(2):251-8. PubMed PMID: 1387846. 9: Smith AD, Smith DL, Zigmond MJ, Amalric M, Koob GF. Differential effects of dopamine receptor subtype blockade on performance of rats in a reaction-time paradigm. Psychopharmacology (Berl). 2000 Mar;148(4):355-60. PubMed PMID: 10928307. 10: Shippenberg TS, Bals-Kubik R, Huber A, Herz A. Neuroanatomical substrates mediating the aversive effects of D-1 dopamine receptor antagonists. Psychopharmacology (Berl). 1991;103(2):209-14. PubMed PMID: 1827526. 11: Witkin JM, Newman AH, Nowak G, Katz JL. Role of dopamine D1 receptors in the lethal effects of cocaine and a quaternary methiodide analog. J Pharmacol Exp Ther. 1993 Oct;267(1):266-74. PubMed PMID: 7901394. 12: Katz JL, Kopajtic TA, Myers KA, Mitkus RJ, Chider M. Behavioral effects of cocaine: interactions with D1 dopaminergic antagonists and agonists in mice and squirrel monkeys. J Pharmacol Exp Ther. 1999 Oct;291(1):265-79. PubMed PMID: 10490913. 13: Lappalainen J, Hietala J, Pohjalainen T, Syvälahti E. Regulation of dopamine D1 receptors by chronic administration of structurally different D1 receptor antagonists: a quantitative autoradiographic study. Eur J Pharmacol. 1992 Jan 14;210(2):195-200. PubMed PMID: 1534766. 14: Schreiber R, Brocco M, Audinot V, Gobert A, Veiga S, Millan MJ. (1-(2,5-dimethoxy-4 iodophenyl)-2-aminopropane)-induced head-twitches in the rat are mediated by 5-hydroxytryptamine (5-HT) 2A receptors: modulation by novel 5-HT2A/2C antagonists, D1 antagonists and 5-HT1A agonists. J Pharmacol Exp Ther. 1995 Apr;273(1):101-12. PubMed PMID: 7714755. 15: Daly SA, Waddington JL. New classes of selective D-1 dopamine receptor antagonist provide further evidence for two directions of D-1:D-2 interaction. Neurochem Int. 1992 Mar;20 Suppl:135S-139S. Review. PubMed PMID: 1365412. 16: Britton DR, Curzon P, Mackenzie RG, Kebabian JW, Williams JE, Kerkman D. Evidence for involvement of both D1 and D2 receptors in maintaining cocaine self-administration. Pharmacol Biochem Behav. 1991 Aug;39(4):911-5. PubMed PMID: 1684870. 17: Rice OV, Gatley SJ, Shen J, Huemmer CL, Rogoz R, DeJesus OT, Volkow ND, Gifford AN. Effects of endogenous neurotransmitters on the in vivo binding of dopamine and 5-HT radiotracers in mice. Neuropsychopharmacology. 2001 Nov;25(5):679-89. PubMed PMID: 11682251. 18: Gnanalingham KK, Hunter AJ, Jenner P, Marsden CD. Selective dopamine antagonist pretreatment on the antiparkinsonian effects of benzazepine D1 dopamine agonists in rodent and primate models of Parkinson's disease--the differential effects of D1 dopamine antagonists in the primate. Psychopharmacology (Berl). 1995 Feb;117(4):403-12. PubMed PMID: 7604140.
PubChem Compound 1-(2-Bromo-4,5-dimethoxybenzyl)-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
Last Modified Mar 14 2022