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MedKoo Cat#: 571089 | Name: Zimelidine

Description:

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

Zimelidine is a serotonin uptake inhibitor formerly used for depression, but was withdrawn worldwide because of the risk of Gullain-Barre syndrome associated with its use.

Chemical Structure

Zimelidine
Zimelidine
CAS#56775-88-3

Theoretical Analysis

MedKoo Cat#: 571089

Name: Zimelidine

CAS#: 56775-88-3

Chemical Formula: C16H17BrN2

Exact Mass: 316.0575

Molecular Weight: 317.23

Elemental Analysis: C, 60.58; H, 5.40; Br, 25.19; N, 8.83

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Related CAS #
No Data
Synonym
Zimelidine; A 23140; A-23140; A23140
IUPAC/Chemical Name
2-Propen-1-amine, 3-(4-bromophenyl)-N,N-dimethyl-3-(3-pyridinyl)-, (Z)-
InChi Key
OYPPVKRFBIWMSX-SXGWCWSVSA-N
InChi Code
InChI=1S/C16H17BrN2/c1-19(2)11-9-16(14-4-3-10-18-12-14)13-5-7-15(17)8-6-13/h3-10,12H,11H2,1-2H3/b16-9-
SMILES Code
CN(C)C/C=C(C1=CC=C(Br)C=C1)\C2=CC=CN=C2
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
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 317.23 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
1: Merideth CH, Feighner JP. A double-blind, controlled evaluation of zimeldine, imipramine and placebo in patients with primary affective disorders. Acta Psychiatr Scand Suppl. 1983;308:70-9. PubMed PMID: 6230897. 2: Bengtsson BO, Wiholm BE, Myrhed M, Wålinder J. Adverse experiences during treatment with zimeldine on special licence in Sweden. Int Clin Psychopharmacol. 1994 Spring;9(1):55-61. PubMed PMID: 8195584. 3: Bjorvatn B, Ursin R. Effects of zimeldine, a selective 5-HT reuptake inhibitor, combined with ritanserin, a selective 5-HT2 antagonist, on waking and sleep stages in rats. Behav Brain Res. 1990 Nov 30;40(3):239-46. PubMed PMID: 2149499. 4: Hindmarch I, Subhan Z, Stoker MJ. The effects of zimeldine and amitriptyline on car driving and psychomotor performance. Acta Psychiatr Scand Suppl. 1983;308:141-6. PubMed PMID: 6230888. 5: Gottfries CG, Grind M, Lundström J, Alling C. Pharmacokinetics of zimeldine in male alcoholics. Acta Pharmacol Toxicol (Copenh). 1986 Aug;59(2):94-102. PubMed PMID: 2946168. 6: Claghorn J, Gershon S, Goldstein BJ. Zimeldine tolerability in comparison to amitriptyline and placebo: findings from a multicentre trial. Acta Psychiatr Scand Suppl. 1983;308:104-14. PubMed PMID: 6230883. 7: Cutler NR, Haxby J, Kay AD, Narang PK, Lesko LJ, Costa JL, Ninos M, Linnoila M, Potter WZ, Renfrew JW, et al. Evaluation of zimeldine in Alzheimer's disease. Cognitive and biochemical measures. Arch Neurol. 1985 Aug;42(8):744-8. PubMed PMID: 2411246. 8: Kristofferson A, Sohl-Akerlund A, Hall E, Bengtsson BO, Ogenstad S, Wålinder J. Effect of zimeldine and its metabolites on [3H]thymidine incorporation in lymphocyte cultures from psychiatric patients with or without a hypersensitivity reaction during zimeldine therapy. Int Clin Psychopharmacol. 1994 Sep;9(3):179-85. PubMed PMID: 7814827. 9: Dehlin O, Björnson G, Lundström J, Nörgård J. Zimeldine to geriatric patients in once daily dosage. A pharmacokinetic and clinical study. Acta Psychiatr Scand. 1984 Feb;69(2):103-11. PubMed PMID: 6230881. 10: Hiramatsu KI, Takahashi R, Mori A, Inoue R, Kazamatsuri H, Murasaki M, Sakuma A. A multicentre double-blind comparative trial of zimeldine and imipramine in primary major depressive disorders. Acta Psychiatr Scand Suppl. 1983;308:41-54. PubMed PMID: 6230895. 11: Bjørkum AA, Neckelmann D, Bjorvatn B, Ursin R. Lesion of descending 5-HT pathways increases zimeldine-induced waking in rats. Physiol Behav. 1995 May;57(5):959-66. PubMed PMID: 7610150. 12: Langlois R, Cournoyer G, de Montigny C, Caillé G. High incidence of multisystemic reactions to zimeldine. Eur J Clin Pharmacol. 1985;28(1):67-71. PubMed PMID: 3157576. 13: Seppälä T, Linnoila M. Effects of zimeldine and other antidepressants on skilled performance: a comprehensive review. Acta Psychiatr Scand Suppl. 1983;308:135-40. Review. PubMed PMID: 6230887. 14: Mulinari S. Divergence and convergence of commercial and scientific priorities in drug development: The case of Zelmid, the first SSRI antidepressant. Soc Sci Med. 2015 Aug;138:217-24. doi: 10.1016/j.socscimed.2015.06.020. Epub 2015 Jun 18. PubMed PMID: 26123880. 15: Seppälä T, Strömberg C, Bergman I. Effects of zimeldine, mianserin and amitriptyline on psychomotor skills and their interaction with ethanol a placebo controlled cross-over study. Eur J Clin Pharmacol. 1984;27(2):181-9. PubMed PMID: 6238829. 16: Bengtsson BO, Zhu J, Thorell LH, Olsson T, Link H, Wålinder J. Effects of zimeldine and its metabolites, clomipramine, imipramine and maprotiline in experimental allergic neuritis in Lewis rats. J Neuroimmunol. 1992 Jul;39(1-2):109-22. PubMed PMID: 1535634. 17: Wahlén A, Westerlund D, Wåhlin-Boll E, Melander A. Influence of food intake on the bioavailability of zimeldine and its active metabolite, norzimeldine. Drug Nutr Interact. 1983;2(3):175-81. PubMed PMID: 6236068. 18: Burrows GD, Norman TR, Marriott PF, Davies B. Zimeldine in depressive illness--efficacy and safety data. Acta Psychiatr Scand Suppl. 1983;308:31-40. PubMed PMID: 6230894. 19: Aberg-Wistedt A, Alvariza M, Bertilsson L, Malmgren R, Wachtmeister H. Alaproclate a novel antidepressant? A biochemical and clinical comparison with zimeldine. Acta Psychiatr Scand. 1985 Mar;71(3):256-68. PubMed PMID: 2580422. 20: Pottage A, Grind MG. Cardiovascular effects of zimeldine. Acta Psychiatr Scand Suppl. 1983;308:125-30. PubMed PMID: 6230885.