Papaverine free base

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MedKoo CAT#: 318453

CAS#: 58-74-2 (free base)

Description: Papaverine free base is discontinued (DEA controlled substance). Papaverine is an opium alkaloid antispasmodic drug used primarily in the treatment of visceral spasm, vasospasm (especially those involving the heart and the brain), and occasionally in the treatment of erectile dysfunction.


Price and Availability

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Pricing updated 2020-07-11. Prices are subject to change without notice.

Papaverine free base is discontinued (DEA controlled substance).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 318453
Name: Papaverine free base
CAS#: 58-74-2 (free base)
Chemical Formula: C20H21NO4
Exact Mass: 339.14706
Molecular Weight: 339.39
Elemental Analysis: C, 70.78; H, 6.24; N, 4.13; O, 18.86


Related CAS #: 58-74-2 (free base)   61-25-6 (HCl)   132-40-1 (nitrite)    

Synonym: Papaverine; Papanerine; Papaverin; Robaxapap; Pavabid; Cerespan; Papaverine Hydrochloride; Pavabid; Pavatym;

IUPAC/Chemical Name: 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline

InChi Key: XQYZDYMELSJDRZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H21NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-8,10-12H,9H2,1-4H3

SMILES Code: COC1=C(C=C(C=C1)CC2=NC=CC3=CC(=C(C=C32)OC)OC)OC


Technical Data

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, not in water

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


References

1: Panigrahy N, Kumar PP, Chirla DK, Vennapusa SR. Papaverine for Ischemia
Following Peripheral Arterial Catheterization in Neonates. Indian Pediatr. 2016
Feb 8;53(2):169. PubMed PMID: 26897158.

2: Nishi T, Kitahara H, Iwata Y, Fujimoto Y, Nakayama T, Takahara M, Sugimoto K,
Kobayashi Y. Efficacy of combined administration of intracoronary papaverine plus
intravenous adenosine 5'-triphosphate in assessment of fractional flow reserve. J
Cardiol. 2016 Jan 22. pii: S0914-5087(15)00403-7. doi:
10.1016/j.jjcc.2015.12.005. [Epub ahead of print] PubMed PMID: 26811149.

3: Fusi F, Manetti F, Durante M, Sgaragli G, Saponara S. The vasodilator
papaverine stimulates L-type Ca(2+) current in rat tail artery myocytes via a
PKA-dependent mechanism. Vascul Pharmacol. 2016 Jan;76:53-61. doi:
10.1016/j.vph.2015.11.041. Epub 2015 Nov 14. PubMed PMID: 26586313.

4: Terriou P, Hans E, Cortvrindt R, Avon C, Charles O, Salzmann J, Lazdunski P,
Giorgetti C. Papaverine as a replacement for pentoxifylline to select thawed
testicular or epididymal spermatozoa before ICSI. Gynecol Obstet Fertil. 2015
Dec;43(12):786-90. doi: 10.1016/j.gyobfe.2015.10.007. Epub 2015 Nov 14. PubMed
PMID: 26584894.

5: Kaneda T, Saito E, Kanda H, Urakawa N, Shimizu K. Effects of papaverine on
carbachol- and high K+ -induced contraction in the bovine abomasum. J Vet Med
Sci. 2015 Oct;77(10):1269-74. doi: 10.1292/jvms.15-0080. Epub 2015 May 28. PubMed
PMID: 26018357; PubMed Central PMCID: PMC4638294.

6: Farrow SC, Facchini PJ. Papaverine 7-O-demethylase, a novel
2-oxoglutarate/Fe(2+)-dependent dioxygenase from opium poppy. FEBS Lett. 2015 Sep
14;589(19 Pt B):2701-6. doi: 10.1016/j.febslet.2015.07.042. Epub 2015 Aug 8.
PubMed PMID: 26264169.

7: Polski A, Iwaniak K, Kasperek R, Modrzewska J, Sobótka-Polska K, Sławińska K,
Poleszak E. Influence of Polymer Type on the Physical Properties and Release
Profile of Papaverine Hydrochloride From Hard Gelatin Capsules. Polim Med. 2015
Jul-Dec;45(2):51-55. PubMed PMID: 26994886.

8: Datta AS, Chattaraj SB, Chakrabortty A, Lahiri SC. Studies on the weak
interactions and CT complex formations between chloranilic acid,
2,3-dichloro-5,6-dicyano-p-benzoquinone, tetracyanoethylene and papaverine in
acetonitrile and their thermodynamic properties, theoretically,
spectrophotometrically aided by FTIR. Spectrochim Acta A Mol Biomol Spectrosc.
2015 Jul 5;146:119-28. doi: 10.1016/j.saa.2015.02.064. Epub 2015 Mar 6. PubMed
PMID: 25813169.

9: Miki K, Fujii K, Fukunaga M, Nishimura M, Horimatsu T, Saita T, Tamaru H,
Imanaka T, Shibuya M, Ohyanagi M, Masuyama T. Assessment of lower limb flow and
adequate intra-arterial papaverine doses to achieve maximal hyperemia in elder
subjects. Cardiovasc Interv Ther. 2015 Jul;30(3):227-33. doi:
10.1007/s12928-014-0307-z. Epub 2014 Nov 13. PubMed PMID: 25392063.

10: Kasperek R, Zimmer Ł, Jawień W, Poleszak E. PHARMACOKINETICS OF DICLOFENAC
SODIUM AND PAPAVERINE HYDROCHLORIDE AFTER ORAL ADMINISTRATION OF TABLETS TO
RABBITS. Acta Pol Pharm. 2015 May-Jun;72(3):527-38. PubMed PMID: 26642661.

11: Reznicek O, Facey SJ, Hauer B. Draft Genome Sequence of a
Papaverine-Degrading, Gram-positive Arthrobacter sp., Isolated from Soil Near
Hohenheim, Germany. Genome Announc. 2015 May 21;3(3). pii: e00422-15. doi:
10.1128/genomeA.00422-15. PubMed PMID: 25999567; PubMed Central PMCID:
PMC4440947.

12: Li H, Zhu X, Yao G, Wang Z. Papaverine improves sublingual blood flow in
patients with septic shock. J Surg Res. 2015 May 1;195(1):271-6. doi:
10.1016/j.jss.2015.01.016. Epub 2015 Jan 13. PubMed PMID: 25676464.

13: Zygourakis CC, Vasudeva V, Lai PM, Kim AH, Wang H, Du R. Transient pupillary
dilation following local papaverine application in intracranial aneurysm surgery.
J Clin Neurosci. 2015 Apr;22(4):676-9. doi: 10.1016/j.jocn.2014.10.016. Epub 2015
Jan 3. PubMed PMID: 25564265.

14: Polski A, Kasperek R, Rogowska M, Iwaniak K, Sobòtka-Polska K, Poleszak E.
Dissolution Studies of Papaverine Hydrochloride from Tablets in Three
Pharmacopoeia Apparatuses. Polim Med. 2015 Jan-Jun;45(1):21-4. PubMed PMID:
26630725.

15: Sajadian S, Vatankhah M, Majdzadeh M, Kouhsari SM, Ghahremani MH, Ostad SN.
Cell cycle arrest and apoptogenic properties of opium alkaloids noscapine and
papaverine on breast cancer stem cells. Toxicol Mech Methods. 2015;25(5):388-95.
doi: 10.3109/15376516.2015.1045656. Epub 2015 May 18. PubMed PMID: 25980655.

16: Nakayama M, Tanaka N, Sakoda K, Hokama Y, Hoshino K, Kimura Y, Ogawa M,
Yamashita J, Kobori Y, Uchiyama T, Aizawa Y, Yamashina A. Papaverine-induced
polymorphic ventricular tachycardia during coronary flow reserve study of
patients with moderate coronary artery disease. Circ J. 2015;79(3):530-6. doi:
10.1253/circj.CJ-14-1118. Epub 2015 Jan 23. PubMed PMID: 25746536.

17: Protasiewicz M, Początek K, Poręba R, Derkacz A, Podgórski M, Gosławska K,
Szymańska-Chabowska A, Mazur G, Mysiak A, Witkowski A. Comparison of the renal
hyperemic effects of papaverine and dopamine in patients with renal artery
stenosis. J Am Soc Hypertens. 2015 Jan;9(1):9-14. doi:
10.1016/j.jash.2014.10.004. Epub 2014 Oct 18. PubMed PMID: 25533109.

18: Baltsavias G, Yella S, Al Shameri RA, Luft A, Valavanis A. Intra-arterial
administration of papaverine during mechanical thrombectomy for acute ischemic
stroke. J Stroke Cerebrovasc Dis. 2015 Jan;24(1):41-7. doi:
10.1016/j.jstrokecerebrovasdis.2014.07.052. Epub 2014 Nov 13. PubMed PMID:
25440359.

19: Kalmár E, Gyuricza A, Kunos-Tóth E, Szakonyi G, Dombi G. Simultaneous
quantification of paracetamol, acetylsalicylic acid and papaverine with a
validated HPLC method. J Chromatogr Sci. 2014 Nov-Dec;52(10):1198-203. doi:
10.1093/chromsci/bmt177. Epub 2013 Dec 15. PubMed PMID: 24344050.

20: Kahramaner Z, Erdemir A, Türkoğlu E, Coşar H, Sütçüoğlu S, Özer EA.
Papaverine intoxication in a newborn: an unusual case report. Turk J Pediatr.
2014 Sep-Oct;56(5):532-4. PubMed PMID: 26022590.