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MedKoo Cat#: 573214 | Name: Apovincamine

Description:

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

Apovincamine is a vinca alkaloid and a chemical precursor of Vinpocetine, a derivative of Vincamine with vasodilating activity.

Chemical Structure

Apovincamine
Apovincamine
CAS#4880-92-6

Theoretical Analysis

MedKoo Cat#: 573214

Name: Apovincamine

CAS#: 4880-92-6

Chemical Formula: C21H24N2O2

Exact Mass: 336.1838

Molecular Weight: 336.44

Elemental Analysis: C, 74.97; H, 7.19; N, 8.33; O, 9.51

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Synonym
Apovincamine, cis-Apovincamine
IUPAC/Chemical Name
methyl (41S,13aS)-13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate
InChi Key
OZDNDGXASTWERN-CTNGQTDRSA-N
InChi Code
1S/C21H24N2O2/c1-3-21-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(18(15)19(21)22)17(13-21)20(24)25-2/h4-5,7-8,13,19H,3,6,9-12H2,1-2H3/t19-,21+/m1/s1
SMILES Code
c12c3c4[C@H]5[N@@](CCC[C@@]5(C=C(n4c2cccc1)C(OC)=O)CC)CC3
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

Preparing Stock Solutions

The following data is based on the product molecular weight 336.44 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
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PMID: 32166194; PMCID: PMC7045535. 4: Feher G, Koltai K, Kesmarky G, Horvath B, Toth K, Komoly S, Szapary L. Effect of parenteral or oral vinpocetine on the hemorheological parameters of patients with chronic cerebrovascular diseases. Phytomedicine. 2009 Mar;16(2-3):111-7. doi: 10.1016/j.phymed.2008.10.014. Epub 2009 Jan 8. PMID: 19135345. 5: Patyar S, Prakash A, Modi M, Medhi B. Role of vinpocetine in cerebrovascular diseases. Pharmacol Rep. 2011;63(3):618-28. doi: 10.1016/s1734-1140(11)70574-6. PMID: 21857073. 6: Vas A, Gulyás B. Eburnamine derivatives and the brain. Med Res Rev. 2005 Nov;25(6):737-57. doi: 10.1002/med.20043. PMID: 16158388. 7: Pickrell JA, Oehme FW, Cash WC. Ototoxicity in dogs and cats. Semin Vet Med Surg Small Anim. 1993 Feb;8(1):42-9. PMID: 8456203. 8: Balestreri R, Fontana L, Astengo F. A double-blind placebo controlled evaluation of the safety and efficacy of vinpocetine in the treatment of patients with chronic vascular senile cerebral dysfunction. J Am Geriatr Soc. 1987 May;35(5):425-30. doi: 10.1111/j.1532-5415.1987.tb04664.x. PMID: 3553281. 9: Czira G, Vereczkey L, Tamás J, Szporny L. Az apovinkaminsav-etilészter (Cavinton) kvantitatív meghatározása humán plazmában és vizeletben [Quantitative determination of apovincamine acid ethyl ester (Cavinton) in human plasma and urine]. Acta Pharm Hung. 1978;48 Suppl:54-5. Hungarian. PMID: 749530. 10: Szatmari SZ, Whitehouse PJ. Vinpocetine for cognitive impairment and dementia. Cochrane Database Syst Rev. 2003;2003(1):CD003119. doi: 10.1002/14651858.CD003119. PMID: 12535455; PMCID: PMC8406981. 11: Vereczkey L. Pharmacokinetics and metabolism of vincamine and related compounds. Eur J Drug Metab Pharmacokinet. 1985 Apr-Jun;10(2):89-103. doi: 10.1007/BF03189702. PMID: 3899662. 12: Reis FL, Adolpho L, Ruiz ALTG, Simionatto E, Dalcol II, Mostardeiro MA, Morel AF. In vitro antiproliferative activity of alkaloids isolated from Tabernaemontana catharinensis A.DC (Apocynaceae). Nat Prod Res. 2022 Nov;36(22):5808-5812. doi: 10.1080/14786419.2021.2017928. Epub 2022 Jan 25. PMID: 35075954. 13: Koyama K, Hirasawa Y, Hosoya T, Hoe TC, Chan KL, Morita H. Alpneumines A-H, new anti-melanogenic indole alkaloids from Alstonia pneumatophora. Bioorg Med Chem. 2010 Jun 15;18(12):4415-21. doi: 10.1016/j.bmc.2010.04.086. Epub 2010 Apr 29. PMID: 20576577. 14: Bönöczk P, Gulyás B, Adam-Vizi V, Nemes A, Kárpáti E, Kiss B, Kapás M, Szántay C, Koncz I, Zelles T, Vas A. Role of sodium channel inhibition in neuroprotection: effect of vinpocetine. Brain Res Bull. 2000 Oct;53(3):245-54. doi: 10.1016/s0361-9230(00)00354-3. PMID: 11113577. 15: El-Sayed SS, El-Yamany MF, Salem HA, El-Sahar AE. New insights into the effects of vinpocetine against neurobehavioral comorbidities in a rat model of temporal lobe epilepsy via the downregulation of the hippocampal PI3K/mTOR signalling pathway. J Pharm Pharmacol. 2021 Mar 27;73(5):626-640. doi: 10.1093/jpp/rgab011. PMID: 33772295. 16: Marzo A, Saccarello ML, Stradi R, Quadro E, Galzigna L, Tartarini S, Reali L. A new phthalidyl derivative of apovincaminic acid: (3 alpha,16 alpha)-eburnamenine-14 carboxylic acid phthalidyl ester (AF 698). A preliminary report on its chemical and pharmacological properties. Arzneimittelforschung. 1982;32(6):601-3. PMID: 7202363. 17: Vereczkey L, Czira G, Tamás J, Szentirmay Z, Botár Z, Szporny L. Pharmacokinetics of vinpocetine in humans. Arzneimittelforschung. 1979;29(6):957-60. PMID: 582791. 18: Feigin VL, Doronin BM, Popova TF, Gribatcheva EV, Tchervov DV. Vinpocetine treatment in acute ischaemic stroke: a pilot single-blind randomized clinical trial. Eur J Neurol. 2001 Jan;8(1):81-5. doi: 10.1046/j.1468-1331.2001.00181.x. PMID: 11509086. 19: Nag S, Krasikova R, Airaksinen AJ, Arakawa R, Petukhovd M, Gulyas B. Synthesis and biological evaluation of [18F]fluorovinpocetine, a potential PET radioligand for TSPO imaging. Bioorg Med Chem Lett. 2019 Aug 15;29(16):2270-2274. doi: 10.1016/j.bmcl.2019.06.037. Epub 2019 Jun 20. PMID: 31257082. 20: Jim HSL, Hoogland AI, Han HS, Culakova E, Heckler C, Janelsins M, Williams GC, Bower J, Cole S, Desta Z, Babilonia MB, Morrow G, Peppone L. A randomized placebo-controlled trial of bupropion for Cancer-related fatigue: Study design and procedures. Contemp Clin Trials. 2020 Apr;91:105976. doi: 10.1016/j.cct.2020.105976. Epub 2020 Mar 5. PMID: 32147571; PMCID: PMC7263969.