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MedKoo Cat#: 318488 | Name: Phenylpropanolamine

Description:

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

Phenylpropanolamine is discontinued (prohibited/illegal in the United States). This product is a sympathomimetic, a psychoactive drug, that acts mainly by causing release of norepinephrine but also has direct agonist activity at some adrenergic receptors. Phenylpropanolamine acts as an alpha-adrenergic receptor and alpha-adrenergic receptor as well as a dopamine receptor D1 partial agonist. It is most commonly used as a nasal vasoconstrictor and an appetite depressant.

Chemical Structure

Phenylpropanolamine
Phenylpropanolamine
CAS#14838-15-4

Theoretical Analysis

MedKoo Cat#: 318488

Name: Phenylpropanolamine

CAS#: 14838-15-4

Chemical Formula: C9H13NO

Exact Mass: 151.0997

Molecular Weight: 151.21

Elemental Analysis: C, 71.49; H, 8.67; N, 9.26; O, 10.58

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
No Data
Synonym
Phenylpropanolamine; Norephedrine; Phenylpropanolamine; Propadrine; Dexatrim; Propagest; Rhindecon; Hydrochloride, Phenylpropanolamine; Phenylpropanolamine Hydrochloride; Prolamine; Propagest;
IUPAC/Chemical Name
(R*,S*)-(1)-alpha-(1-Aminoethyl)benzyl alcohol
InChi Key
DLNKOYKMWOXYQA-CBAPKCEASA-N
InChi Code
InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1
SMILES Code
C[C@H](N)[C@H](O)c1ccccc1
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 151.21 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: Chennakesava Rao K, Easwaramoorthi K, Arun Y, Balachandran C, Muralidhara Rao KS, Govindhan M, Emi N, Prakasam T, Perumal PT. Synthesis of BF₃ catalyzed Mannich derivatives with excellent ee from phenylpropanolamine, study of their antimicrobial activity and molecular docking. Bioorg Med Chem Lett. 2015 Oct 1;25(19):4232-8. doi: 10.1016/j.bmcl.2015.07.096. Epub 2015 Aug 6. PubMed PMID: 26296475. 2: Segev G, Westropp JL, Kulik C, Lavy E. Changes in blood pressure following escalating doses of phenylpropanolamine and a suggested protocol for monitoring. Can Vet J. 2015 Jan;56(1):39-43. PubMed PMID: 25565712; PubMed Central PMCID: PMC4266053. 3: Hsieh YS, Chen PN, Yu CH, Liao JM, Kuo DY. Inhibiting neuropeptide Y Y1 receptor modulates melanocortin receptor- and NF-κB-mediated feeding behavior in phenylpropanolamine-treated rats. Horm Behav. 2013 Jun;64(1):95-102. doi: 10.1016/j.yhbeh.2013.05.005. Epub 2013 May 22. PubMed PMID: 23707533. 4: Hsieh YS, Kuo MH, Chen PN, Kuo DY. The identification of neuropeptide Y receptor subtype involved in phenylpropanolamine-induced increase in oxidative stress and appetite suppression. Neuromolecular Med. 2013 Mar;15(1):159-68. doi: 10.1007/s12017-012-8206-x. Epub 2012 Nov 20. PubMed PMID: 23179670. 5: Hsieh YS, Chen PN, Kuo MH, Kuo DY. Neuropeptide Y Y1 receptor knockdown can modify glutathione peroxidase and c-AMP response element-binding protein in phenylpropanolamine-treated rats. Arch Toxicol. 2013 Mar;87(3):469-79. doi: 10.1007/s00204-012-0947-7. Epub 2012 Oct 4. PubMed PMID: 23052195. 6: Yakoot M. Phenylpropanolamine and the hemorrhagic stroke: A new search for the culprit. J Pharmacol Pharmacother. 2012 Jan;3(1):4-6. doi: 10.4103/0976-500X.92491. PubMed PMID: 22368408; PubMed Central PMCID: PMC3284035. 7: Peterson KL, Lee JA, Hovda LR. Phenylpropanolamine toxicosis in dogs: 170 cases (2004?2009). J Am Vet Med Assoc. 2011 Dec 1;239(11):1463-9. doi: 10.2460/javma.239.11.1463. PubMed PMID: 22087722. 8: Claeys S, Rustichelli F, Noël S, Hamaide A. Clinical evaluation of a single daily dose of phenylpropanolamine in the treatment of urethral sphincter mechanism incompetence in the bitch. Can Vet J. 2011 May;52(5):501-5. PubMed PMID: 22043069; PubMed Central PMCID: PMC3078002. 9: Gambaro V, Arnoldi S, Colombo ML, Dell'Acqua L, Guerrini K, Roda G. Determination of the active principles of Catha Edulis: quali-quantitative analysis of cathinone, cathine, and phenylpropanolamine. Forensic Sci Int. 2012 Apr 10;217(1-3):87-92. doi: 10.1016/j.forsciint.2011.09.028. Epub 2011 Oct 22. PubMed PMID: 22024653. 10: Kuo DY, Chen PN, Chu SC, Hsieh YS. Knocking down the transcript of NF-kappaB modulates the reciprocal regulation of endogenous antioxidants and feeding behavior in phenylpropanolamine-treated rats. Arch Toxicol. 2012 Mar;86(3):453-63. doi: 10.1007/s00204-011-0761-7. Epub 2011 Oct 12. PubMed PMID: 21989786. 11: Kawanabe T, Tanaka R, Sakaguchi Y, Akiyama O, Shimura H, Yasumoto Y, Ito M, Hattori N, Tanaka S. Posterior reversible encephalopathy syndrome complicating intracranial hemorrhage after phenylpropanolamine exposure. Neurol Med Chir (Tokyo). 2011;51(8):582-5. PubMed PMID: 21869581. 12: Noël S, Massart L, Hamaide A. Urodynamic and haemodynamic effects of a single oral administration of ephedrine or phenylpropanolamine in continent female dogs. Vet J. 2012 Apr;192(1):89-95. doi: 10.1016/j.tvjl.2011.05.003. Epub 2011 Jun 28. PubMed PMID: 21715199. 13: Suwalsky M, Zambrano P, Mennickent S, Villena F, Sotomayor CP, Aguilar LF, Bolognin S. Effects of phenylpropanolamine (PPA) on in vitro human erythrocyte membranes and molecular models. Biochem Biophys Res Commun. 2011 Mar 18;406(3):320-5. doi: 10.1016/j.bbrc.2011.01.117. Epub 2011 Feb 12. PubMed PMID: 21320467. 14: Drug Enforcement Administration, Department of Justice. Removal of thresholds for the List I chemicals pseudoephedrine and phenylpropanolamine. Final rule. Fed Regist. 2010 Jul 7;75(129):38915-22. PubMed PMID: 20608288. 15: Kuo DY, Yang SF, Chu SC, Chen CH, Chen PN, Hsieh YS. The effect of protein kinase C-delta knockdown on anti-free radical enzyme and neuropeptide Y gene expression in phenylpropanolamine-treated rats. J Neurochem. 2010 Aug;114(4):1217-30. doi: 10.1111/j.1471-4159.2010.06843.x. Epub 2010 Jun 1. PubMed PMID: 20533995. 16: Walash MI, El-Enany N, Saad S. A New Spectrophotometric Method for Determination of Phenylpropanolamine HCl in its Pharmaceutical Formulations via Reaction with 2,3,5,6-tetrachloro-1,4-benzoquinone. Int J Biomed Sci. 2010 Jun;6(2):150-7. PubMed PMID: 23675189; PubMed Central PMCID: PMC3614736. 17: Drug Enforcement Administration (DEA), Justice. Information on foreign chain of distribution for ephedrine, pseudoephedrine, and phenylpropanolamine. Final rule. Fed Regist. 2010 Mar 5;75(43):10168-72. PubMed PMID: 20383917. 18: Drug Enforcement Administration (DEA), Justice. Registration requirements for importers and manufacturers of prescription drug products containing ephedrine, pseudoephedrine, or phenylpropanolamine. Final rule. Fed Regist. 2010 Feb 1;75(20):4973-82. PubMed PMID: 20352663. 19: Noël S, Cambier C, Baert K, Gustin P, Denooz R, Massart L, Hamaide A. Combined pharmacokinetic and urodynamic study of the effects of oral administration of phenylpropanolamine in female Beagle dogs. Vet J. 2010 May;184(2):201-7. doi: 10.1016/j.tvjl.2009.01.026. Epub 2009 Mar 17. PubMed PMID: 19282207. 20: Kuo DY, Yang SF, Chu SC, Chen CH, Hsieh YS. Roles of protein kinase Calpha isozyme in the regulation of oxidative stress and neuropeptide Y gene expression in phenylpropanolamine-mediated appetite suppression. J Neurochem. 2009 Mar;108(6):1495-506. doi: 10.1111/j.1471-4159.2009.05909.x. Epub 2009 Jan 22. PubMed PMID: 19183253.

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