Butaclamol HCl

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 593126

CAS#: 36504-94-6 (HCl)

Description: Butaclamol, also known as AY-23,028, is a typical antipsychotic which was never marketed. Sold as the hydrochloride salt for use in research, the compound acts as a dopamine receptor antagonist.


Chemical Structure

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Butaclamol HCl
CAS# 36504-94-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 593126
Name: Butaclamol HCl
CAS#: 36504-94-6 (HCl)
Chemical Formula: C25H32ClNO
Exact Mass: 0.00
Molecular Weight: 397.990
Elemental Analysis: C, 75.45; H, 8.10; Cl, 8.91; N, 3.52; O, 4.02

Price and Availability

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25mg USD 380
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Related CAS #: 36504-93-5 (free base)   36504-94-6 (HCl)   51152-91-1 (free base)    

Synonym: Butaclamol hydrochloride; AY-23,028; AY 23,028; AY23,028; AY-23028; AY 23028; AY23028; (-)-Butaclamol; Butaclamol; Butaclamol, (-)- l; (-)Butaclamol; l-Butaclamol

IUPAC/Chemical Name: (3R,4aR,13bR)-3-(1,1-Dimethylethyl)-2,3,4,4a,8,9,13b,14-octahydro-1H-benzo[6,7]cyclohepta[1,2,3-de]pyrido[2,1-a]isoquinolin-3-ol hydrochloride

InChi Key: QZRUMKUMFJJARD-OMMJFLKZSA-N

InChi Code: InChI=1S/C25H31NO.ClH/c1-24(2,3)25(27)13-14-26-16-21-19-9-5-4-7-17(19)11-12-18-8-6-10-20(23(18)21)22(26)15-25;/h4-10,21-22,27H,11-16H2,1-3H3;1H/t21-,22-,25-;/m1./s1

SMILES Code: [H][C@]12C3=C(C=CC=C3[C@](C[C@@](O)(C(C)(C)C)CC4)([H])N4C2)CCC5=C1C=CC=C5.[H]Cl

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 397.99 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Stefan-van Staden RI, Nhlapo NS, van Staden JF, Aboul-Enein HY. Enantioanalysis of (-)butaclamol using vancomycin and teicoplanin as chiral selectors. Comb Chem High Throughput Screen. 2010 Sep;13(8):690-3. PubMed PMID: 20426737.

2: Aboul-Enein HY, Hefnawy MM. Chiral analysis of butaclamol enantiomers in human plasma by HPLC using a macrocyclic antibiotic (vancomycin) chiral stationary phase and solid phase extraction. Chirality. 2004 Mar;16(3):147-52. PubMed PMID: 14770410.

3: Varga A, Sabat R, Mucsi I, Flores VC, Kaiser HE, Molnár J. Effects of butaclamol, clopenthixol, mepromazine and cannabinol stereoisomers on apoptosis induction. Anticancer Res. 2001 Jul-Aug;21(4A):2709-12. PubMed PMID: 11724344.

4: Casarotto MG, Craik DJ, Lloyd EJ. NMR studies of the conformational interconversion of butaclamol in solution. J Med Chem. 1991 Jul;34(7):2043-9. PubMed PMID: 1712393.

5: Casarotto MG, Craik DJ, Lloyd EJ, Partridge AC. An NMR and theoretical study of the conformation and internal flexibility of butaclamol hydrochloride. J Med Chem. 1991 Jul;34(7):2036-43. PubMed PMID: 1712392.

6: Bissette G, Dauer WT, Kilts CD, O'Connor L, Nemeroff CB. The effect of the stereoisomers of butaclamol on neurotensin content in discrete regions of the rat brain. Neuropsychopharmacology. 1988 Dec;1(4):329-35. PubMed PMID: 2472151.

7: Collu R, Bouvier C, Basak A, Dugas H. Dopaminergic activity of four analogs of butaclamol. Pharmacol Res Commun. 1985 Dec;17(12):1153-7. PubMed PMID: 2419927.

8: Chrzanowski FA, McGrogan BA, Maryanoff BE. The pKa of butaclamol and the mode of butaclamol binding to central dopamine receptors. J Med Chem. 1985 Mar;28(3):399-400. PubMed PMID: 2579238.

9: Mineeva MF, Raevskiĭ KS. [Effect of butaclamol enantiomers on hypothalamic tyrosine hydroxylase in the rat brain]. Biull Eksp Biol Med. 1984 Oct;98(10):453-6. Russian. PubMed PMID: 6208950.

10: Froimowitz M, Matthysse S. Conformational properties of butaclamol and isobutaclamol. Regularities in the structures of semirigid neuroleptics. Mol Pharmacol. 1983 Sep;24(2):243-50. PubMed PMID: 6193405.

11: Spedding M, Berg C. Stereospecific blockade of alpha 2-adrenoceptors by (+)-butaclamol: implications for the characterization of dopamine receptors. J Pharm Pharmacol. 1982 Jan;34(1):56-8. PubMed PMID: 6174723.

12: Brodde OE, Freistühler J, Meyer FJ. Stereospecific antagonism by d-butaclamol of dopamine-induced relaxation of the isolated rabbit mesenteric artery. J Cardiovasc Pharmacol. 1981 Jul-Aug;3(4):828-37. PubMed PMID: 6167812.

13: Lin CW, Maayani S, Wilk S. [3H]dihydroergocryptine binding to bovine striatal membranes defined by a low d-butaclamol concentration: antagonism by substituted benzamides. Biochem Pharmacol. 1981 Jun 1;30(11):1305-14. PubMed PMID: 6168265.

14: Gnegy ME, Lau YS. Calmodulin release from striatal membranes after acute and chronic treatment with butaclamol. Adv Biochem Psychopharmacol. 1980;24:147-51. PubMed PMID: 6157308.

15: Philipp AH, Humber LG, Voith K. Mapping the dopamine receptor. 2. Features derived from modifications in the rings A/B region of the neuroleptic butaclamol. J Med Chem. 1979 Jul;22(7):768-73. PubMed PMID: 571917.

16: Humber LG, Bruderlein FT, Philipp AH, Götz M. Mapping the dopamine receptor. 1. Features derived from modifications in ring E of the neuroleptic butaclamol. J Med Chem. 1979 Jul;22(7):761-7. PubMed PMID: 571916.

17: Kukla MJ, Bloss JL, Brougham LR. Use of the butaclamol template in a search for antipsychotic agents with lessened side effects. J Med Chem. 1979 Apr;22(4):401-6. PubMed PMID: 34721.

18: Pugsley TA, Lippmann W. Effects of chlorine substituents on the benzene rings of an analogue of the antipsychotic drug butaclamol on the interaction with dopamine and muscarinic receptors in rat brain. J Pharm Pharmacol. 1979 Jan;31(1):47-9. PubMed PMID: 32368.

19: Humber LG, Sideridis N, Asselin AA, Bruderlein FT, Voith K. Neuroleptics related to butaclamol. An investigation of the effects of chlorine substituents on the aromatic rings. J Med Chem. 1978 Dec;21(12):1225-31. PubMed PMID: 31480.

20: Voith K, Bruderlein FT, Humber LG. Neuroleptics related to butaclamol. Synthesis and some psychopharmacological effects of a series of 3-aryl analogues. J Med Chem. 1978 Jul;21(7):694-8. PubMed PMID: 27637.