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MedKoo Cat#: 573108 | Name: Alniditan

Description:

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

Alniditan is a 5-HT1B/D receptor agonist that may be used in the treatment of migraines. Alniditan selectively constricts porcine carotid arteriovenous anastomoses via 5-HT1B/1D receptors. alniditan is a potent agonist at h5-HT1D alpha and h5-HT1D beta receptors; its properties probably underlie its cranial vasoconstrictive and antimigraine properties.

Chemical Structure

Alniditan
Alniditan
CAS#152317-89-0 (free base)

Theoretical Analysis

MedKoo Cat#: 573108

Name: Alniditan

CAS#: 152317-89-0 (free base)

Chemical Formula: C17H26N4O

Exact Mass: 302.2107

Molecular Weight: 302.42

Elemental Analysis: C, 67.52; H, 8.67; N, 18.53; O, 5.29

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
155428-00-5 (HCl) 152317-89-0 (free base)
Synonym
Alniditan; R 91274; R91274; R-91274; R091274, R-091274, R 091274, JNJ 16384810-AAC; JNJ 16384810; JNJ-16384810; JNJ16384810;
IUPAC/Chemical Name
2-((3-(((R)-2-Chromanylmethyl)amino)propyl)amino)-1,4,5,6-tetrahydropyrimidine
InChi Key
QVSXOXCYXPQXMF-OAHLLOKOSA-N
InChi Code
1S/C17H26N4O/c1-2-6-16-14(5-1)7-8-15(22-16)13-18-9-3-10-19-17-20-11-4-12-21-17/h1-2,5-6,15,18H,3-4,7-13H2,(H2,19,20,21)/t15-/m1/s1
SMILES Code
C1c2c(O[C@H](CNCCCNC3=NCCCN3)C1)cccc2
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 302.42 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: Do TP, Guo S, Ashina M. Correction to: Therapeutic novelties in migraine: new drugs, new hope? J Headache Pain. 2019 May 17;20(1):55. doi: 10.1186/s10194-019-1013-0. Erratum for: J Headache Pain. 2019 Apr 17;20(1):37. PMID: 31100999; PMCID: PMC6734468. 2: Rapoport AM. The therapeutic future in headache. Neurol Sci. 2012 May;33 Suppl 1:S119-25. doi: 10.1007/s10072-012-1056-3. PMID: 22644186. 3: Nugroho AK, Della-Pasqua O, Danhof M, Bouwstra JA. Compartmental modeling of transdermal iontophoretic transport II: in vivo model derivation and application. Pharm Res. 2005 Mar;22(3):335-46. doi: 10.1007/s11095-004-1870-2. PMID: 15835738. 4: Janssen P, Tack J, Sifrim D, Meulemans AL, Lefebvre RA. Influence of 5-HT1 receptor agonists on feline stomach relaxation. Eur J Pharmacol. 2004 May 25;492(2-3):259-67. doi: 10.1016/j.ejphar.2004.03.054. PMID: 15178373. 5: Goadsby PJ, Classey JD. Evidence for serotonin (5-HT)1B, 5-HT1D and 5-HT1F receptor inhibitory effects on trigeminal neurons with craniovascular input. Neuroscience. 2003;122(2):491-8. doi: 10.1016/s0306-4522(03)00570-0. PMID: 14614913. 6: Newman-Tancredi A, Cussac D, Marini L, Touzard M, Millan MJ. h5-HT(1B) receptor-mediated constitutive Galphai3-protein activation in stably transfected Chinese hamster ovary cells: an antibody capture assay reveals protean efficacy of 5-HT. Br J Pharmacol. 2003 Mar;138(6):1077-84. doi: 10.1038/sj.bjp.0705140. PMID: 12684263; PMCID: PMC1573751. 7: Bhalla P, Sharma HS, Wurch T, Pauwels PJ, Saxena PR. Molecular cloning and expression of the porcine trigeminal ganglion cDNA encoding a 5-ht(1F) receptor. Eur J Pharmacol. 2002 Feb 1;436(1-2):23-33. doi: 10.1016/s0014-2999(01)01605-3. PMID: 11834243. 8: Diener HC, Tfelt-Hansen P, de Beukelaar F, Ferrari MD, Olesen J, Dahlöf C, Mathew N; Study Group. The efficacy and safety of sc alniditan vs. sc sumatriptan in the acute treatment of migraine: a randomized, double-blind, placebo-controlled trial. Cephalalgia. 2001 Jul;21(6):672-9. doi: 10.1046/j.0333-1024.2001.00222.x. PMID: 11531899. 9: Diener HC, Louis P, Schellens R, De Beukelaar F; Study Group. Treatment of migraine attacks with intranasal alniditan: an open study. Cephalalgia. 2001 Mar;21(2):140-4. doi: 10.1046/j.1468-2982.2001.00182.x. PMID: 11422097. 10: Boers PM, Donaldson C, Zagami AS, Lambert GA. 5-HT(1A) and 5-HT(1B/1D) receptors are involved in the modulation of the trigeminovascular system of the cat: a microiontophoretic study. Neuropharmacology. 2000 Jul 24;39(10):1833-47. doi: 10.1016/s0028-3908(99)00241-5. PMID: 10884564. 11: Bouchelet I, Case B, Olivier A, Hamel E. No contractile effect for 5-HT1D and 5-HT1F receptor agonists in human and bovine cerebral arteries: similarity with human coronary artery. Br J Pharmacol. 2000 Feb;129(3):501-8. doi: 10.1038/sj.bjp.0703081. PMID: 10711348; PMCID: PMC1571865. 12: Limmroth V, Bischoff A, Fetscher C, Wermelskirchen D, Diener H, Michel MC. Effects of alniditan on neurogenic oedema in the rat dura mater and on contraction of rat basilar artery. Eur J Pharmacol. 1999 Oct 8;382(2):103-9. doi: 10.1016/s0014-2999(99)00602-0. PMID: 10528144. 13: Bonaventure P, Umans L, Bakker MH, Cras P, Langlois X, Luyten WH, Megens AA, Serneels L, Van Leuven F, Leysen JE. Humanization of mouse 5-hydroxytryptamine1B receptor gene by homologous recombination: in vitro and in vivo characterization. Mol Pharmacol. 1999 Jul;56(1):54-67. doi: 10.1124/mol.56.1.54. PMID: 10385684. 14: Roon KI, Soons PA, Uitendaal MP, de Beukelaar F, Ferrari MD. Pharmacokinetic profile of alniditan nasal spray during and outside migraine attacks. Br J Clin Pharmacol. 1999 Mar;47(3):285-90. doi: 10.1046/j.1365-2125.1999.00894.x. PMID: 10215753; PMCID: PMC2014228. 15: Jadoul A, Lecouturier N, Mesens J, Caers W, Préat V. Transdermal alniditan delivery by skin electroporation. J Control Release. 1998 Aug 14;54(3):265-72. doi: 10.1016/s0168-3659(97)00195-8. PMID: 9766246. 16: De Vries P, Willems EW, Heiligers JP, Villalón CM, Saxena PR. The antimigraine agent alniditan selectively constricts porcine carotid arteriovenous anastomoses via 5-HT1B/1D receptors. Eur J Pharmacol. 1998 Jun 19;351(2):193-201. doi: 10.1016/s0014-2999(98)00301-x. PMID: 9687003. 17: Lesage AS, Wouters R, Van Gompel P, Heylen L, Vanhoenacker P, Haegeman G, Luyten WH, Leysen JE. Agonistic properties of alniditan, sumatriptan and dihydroergotamine on human 5-HT1B and 5-HT1D receptors expressed in various mammalian cell lines. Br J Pharmacol. 1998 Apr;123(8):1655-65. doi: 10.1038/sj.bjp.0701766. PMID: 9605573; PMCID: PMC1565323. 18: Bonaventure P, Voorn P, Luyten WH, Jurzak M, Schotte A, Leysen JE. Detailed mapping of serotonin 5-HT1B and 5-HT1D receptor messenger RNA and ligand binding sites in guinea-pig brain and trigeminal ganglion: clues for function. Neuroscience. 1998 Jan;82(2):469-84. doi: 10.1016/s0306-4522(97)00302-3. PMID: 9466454. 19: Schoenen J. Acute migraine therapy: the newer drugs. Curr Opin Neurol. 1997 Jun;10(3):237-43. doi: 10.1097/00019052-199706000-00012. Erratum in: Curr Opin Neurol 1997 Oct;10(5):following 136. PMID: 9229132. 20: Newman-Tancredi A, Conte C, Chaput C, Verrièle L, Audinot-Bouchez V, Lochon S, Lavielle G, Millan MJ. Agonist activity of antimigraine drugs at recombinant human 5-HT1A receptors: potential implications for prophylactic and acute therapy. Naunyn Schmiedebergs Arch Pharmacol. 1997 Jun;355(6):682-8. doi: 10.1007/pl00005000. PMID: 9205951.