Beclamide
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MedKoo CAT#: 535292

CAS#: 501-68-8

Description: Beclamide is a drug that possesses anticonvulsant activity. It is no longer used. Beclamide is possibly metabolized to 3-chloropropanoic acid in vivo, which binds to the GHB receptor. It has been used as a sedative and as an anticonvulsant. It was studied in the 1950s for its anticonvulsant properties, as a treatment for generalised tonic-clonic seizures. It was not effective for absence seizures. Interest in the drug resumed in the 1990s for its psychiatric properties as an adjunct in the treatment of schizophrenia. While not classified as a DEA controlled substance in the United States, this product can only be sold STRICTLY to universities and research institutions. This product will not be sold to individuals or shipped to residential addresses.


Chemical Structure

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Beclamide
CAS# 501-68-8

Theoretical Analysis

MedKoo Cat#: 535292
Name: Beclamide
CAS#: 501-68-8
Chemical Formula: C10H12ClNO
Exact Mass: 197.0607
Molecular Weight: 197.662
Elemental Analysis: C, 60.77; H, 6.12; Cl, 17.93; N, 7.09; O, 8.09

Price and Availability

Size Price Availability Quantity
100.0mg USD 550.0 2 Weeks
200.0mg USD 950.0 2 Weeks
500.0mg USD 1650.0 2 Weeks
1.0g USD 2450.0 2 Weeks
2.0g USD 4450.0 2 Weeks
5.0g USD 6950.0 2 Weeks
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Synonym: Beclamide; Chloracon, Hibicon, Posedrine, Nydrane, Seclar, and other names;

IUPAC/Chemical Name: N-Benzyl-3-chloropropionamide

InChi Key: JPYQFYIEOUVJDU-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H12ClNO/c11-7-6-10(13)12-8-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)

SMILES Code: O=C(NCC1=CC=CC=C1)CCCl

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

Product Data:

Biological target: Beclamide is a drug that possesses anticonvulsant activity.
In vitro activity: TBD
In vivo activity: The anti-aggressive effects of orally administered beclamide (N-Benzyl-beta-chloropropionamide) were studied in male albino mice which were individually isolated for a 28-day period. Beclamide (50-250 mg kg-1 p.o.) caused an overall dose-dependent increase in the attack onset latency, a reduction in the percentage of animals attacking and the mean number of attacks/animal for this model of aggression. In addition, the highest dose of beclamide (250 mg kg-1 p.o.) did not significantly modify locomotor activity in mice. It was concluded that beclamide induced anti-aggressive effects at non-sedative doses. This anti-aggressive action was thought be at least partially mediated, through a beclamide-induced release of 5-HT from presynaptic sites. Reference: J Pharm Pharmacol. 1988 Dec;40(12):891-3. https://academic.oup.com/jpp/article-abstract/40/12/891/6176493?redirectedFrom=fulltext

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 70.0 354.14
Ethanol 40.0 202.37

Preparing Stock Solutions

The following data is based on the product molecular weight 197.662 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: 1. Darmani NA, Sewell RD, Nicholls PJ. Effects of beclamide on isolation-induced aggression and locomotor activity in mice. J Pharm Pharmacol. 1988 Dec;40(12):891-3. doi: 10.1111/j.2042-7158.1988.tb06297.x. PMID: 2907587.
In vitro protocol: TBD
In vivo protocol: 1. Darmani NA, Sewell RD, Nicholls PJ. Effects of beclamide on isolation-induced aggression and locomotor activity in mice. J Pharm Pharmacol. 1988 Dec;40(12):891-3. doi: 10.1111/j.2042-7158.1988.tb06297.x. PMID: 2907587.

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1: Ahmadi M, Nicholls PJ, Smith HJ, Spencer PS, Preet-Ryatt MS, Spragg BP. Metabolism of beclamide after a single oral dose in man: quantitative studies. J Pharm Pharmacol. 1995 Oct;47(10):876-8. doi: 10.1111/j.2042-7158.1995.tb05757.x. PMID: 8583359.

2: Raptis C, Garcia-Borreguero D, Weber MM, Dose M, Bremer D, Emrich HM. Anticonvulsants as adjuncts for the neuroleptic treatment of schizophrenic psychoses: a clinical study with beclamide. Acta Psychiatr Scand. 1990 Feb;81(2):162-7. doi: 10.1111/j.1600-0447.1990.tb06472.x. PMID: 2183543.

3: Darmani NA, Sewell RD, Nicholls PJ. Acute effects of beclamide on brain regional monoamine concentrations, their metabolites and radioligand binding studies. J Pharm Pharmacol. 1991 Jun;43(6):425-9. doi: 10.1111/j.2042-7158.1991.tb03502.x. PMID: 1717674.

4: WILSON J, WALTON JN, NEWELL DJ. Beclamide in intractable epilepsy: a controlled trial. Br Med J. 1959 May 16;1(5132):1275-8. doi: 10.1136/bmj.1.5132.1275. PMID: 13651708; PMCID: PMC1993459.

5: Ozer AY, Hincal AA. Studies on the masking of unpleasant taste of beclamide: microencapsulation and tabletting. J Microencapsul. 1990 Jul-Sep;7(3):327-39. doi: 10.3109/02652049009021843. PMID: 2384836.

6: Movsisyan M, Heugebaert TSA, Roman BI, Dams R, Van Campenhout R, Conradi M, Stevens CV. Atom- and Mass-economical Continuous Flow Production of 3-Chloropropionyl Chloride and its Subsequent Amidation. Chemistry. 2018 Aug 9;24(45):11779-11784. doi: 10.1002/chem.201802208. Epub 2018 Jul 13. PMID: 29879290.

7: Darmani NA, Sewell RD, Nicholls PJ. Effects of beclamide on isolation-induced aggression and locomotor activity in mice. J Pharm Pharmacol. 1988 Dec;40(12):891-3. doi: 10.1111/j.2042-7158.1988.tb06297.x. PMID: 2907587.

8: Darmani NA, Sewell RD, Hasan MY, Nicholls PJ. Comparison of the inhibitory action of aminobeclamide and beclamide on socially offensive behaviour. J Pharm Pharmacol. 1990 Jun;42(6):447-9. doi: 10.1111/j.2042-7158.1990.tb06591.x. PMID: 1979631.

9: Leach H, Lewis M, Luscombe DK, Nicholls PJ. Studies of plasma levels and the excretion of beclamide in normal human subjects [proceedings]. Br J Clin Pharmacol. 1975 Aug;2(4):377P-378P. PMID: 1234008.

10: Nicholls PJ, Ross MS, Luscombe DK. Metabolism of beclamide, N-benzyl-3-chloropropionamide, in man. Xenobiotica. 1979 Feb;9(2):129-40. doi: 10.3109/00498257909038713. PMID: 433311.

11: Jones OP, Leach H, Luscombe DK, Nicholls PJ. A simple method for the determination of beclamide in plasma by gas chromatography. Br J Clin Pharmacol. 1975 Aug;2(4):364-5. doi: 10.1111/j.1365-2125.1975.tb02788.x. PMID: 1233999; PMCID: PMC1402593.

12: Sawaya MC, Horton RW, Meldrum BS. Effects of anticonvulsant drugs on the cerebral enzymes metabolizing GABA. Epilepsia. 1975 Nov;16(4):649-55. doi: 10.1111/j.1528-1157.1975.tb04747.x. PMID: 9890792.

13: Rydzynski Z, Kocur J, Czarnecka E. Effets du béclamide sur le comportement des animaux [Effects of beclamide on animal behavior]. Therapie. 1977 May- Jun;32(3):365-74. French. PMID: 563113.

14: Luscombe DK, Nicholls PJ. Proceedings: Potential tolerance to beclamide and related drug interactions. J Pharm Pharmacol. 1975 Dec;27 Suppl?-2:18P. PMID: 2690.

15: Skerritt JH, Johnston GA. Inhibition of amino acid transmitter release from rat brain slices by phenytoin and related anticonvulsants. Clin Exp Pharmacol Physiol. 1983 Sep-Oct;10(5):527-33. doi: 10.1111/j.1440-1681.1983.tb00221.x. PMID: 6139193.

16: Cornelis J, Chaillet F. Détermination simultanée par chromatographie liquide haute performance de huit antiépileptiques et sédatifs dans le plasma. Utilisation d'un système à compression radiale de la colonne [Simultaneous high performance liquid chromatographic determination of 8 anti-epileptics and sedatives in plasma. Use of a radial compression column system]. Ann Biol Clin (Paris). 1984;42(4):295-9. French. PMID: 6497073.

17: KAYE N, JONES IH, WARRIER GK. Nydrane as an anticonvulsant. Br Med J. 1959 Mar 7;1(5122):627-9. doi: 10.1136/bmj.1.5122.627. PMID: 13629072; PMCID: PMC1992701.

18: Darling CM, Pryor P. Anticonvulsant activity of alkyl-substituted N-benzylcyanoacetamides. J Pharm Sci. 1979 Jan;68(1):108-10. doi: 10.1002/jps.2600680137. PMID: 758443.

19: GANIDEL G, MERVEILLE P, QUEVAUVILBER A, THUILLIER J. Traitement de quelques cas d'épilepsie par un nouvel antiépileptique: la-N-benzyl beta chloro propionamide [N-benzyl-3-chloropropionamide, a new anticonvulsant, in therapy of some cases of epilepsy]. Ann Med Psychol (Paris). 1953 Nov;111(2 4):531-6. Undetermined Language. PMID: 13125052.

20: ARTEMENKO GN, KEVERINA NV. [Chloracon--an antiepileptic drug]. Med Prom SSSR. 1961 Dec;12:57. Russian. PMID: 13862637.

Beclamide

100.0mg / USD 550.0