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MedKoo Cat#: 413689 | Name: Papaverine adenylate

Description:

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

Papaverine adenylate is a salt of papaverine, an alkaloid found in opium. It is a vasodilating agent used for treating certain conditions that are accompanied by smooth muscle spasms (eg, blood vessel, urinary, gallbladder, or intestinal spasm). This product is discontinued (DEA controlled substance, Schedule II).

Chemical Structure

Papaverine adenylate
Papaverine adenylate
CAS#39024-96-9 (adenylate)

Theoretical Analysis

MedKoo Cat#: 413689

Name: Papaverine adenylate

CAS#: 39024-96-9 (adenylate)

Chemical Formula: C30H35N6O11P

Exact Mass: 686.2101

Molecular Weight: 686.61

Elemental Analysis: C, 52.48; H, 5.14; N, 12.24; O, 25.63; P, 4.51

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
39024-96-9 (adenylate) 58-74-2 (free base) 61-25-6 (HCl) 132-40-1 (nitrite)
Synonym
Papaverine adenylate; Dicertan; EINECS 254-252-3
IUPAC/Chemical Name
5'-Adenylic acid, compd. with 1-((3,4-dimethoxyphenyl)methyl)-6,7-dimethoxyisoquinoline (1:1)
InChi Key
BAJNONMTXYJRMJ-LPEHXXKESA-N
InChi Code
InChI=1S/C20H21NO4.C10H14N5O7P/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;11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h5-8,10-12H,9H2,1-4H3;2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t;4-,6-,7-,10-/m.1/s1
SMILES Code
O=P(O)(OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C(N=CN=C32)N)O1)O)O)O.COC4=CC5=C(C=C4OC)C=CN=C5CC6=CC=C(OC)C(OC)=C6
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 686.61 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: 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.

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