Synonym
MDL72274; MDL-72274; MDL 72274; MDL72274A; MDL-72274A; MDL 72274A; MDL72274 HCl
IUPAC/Chemical Name
(E)-3-chloro-2-phenylprop-2-en-1-amine hydrochloride
InChi Key
KSVZCVSJFUUXGT-BORNJIKYSA-N
InChi Code
InChI=1S/C9H10ClN.ClH/c10-6-9(7-11)8-4-2-1-3-5-8;/h1-6H,7,11H2;1H/b9-6-;
SMILES Code
NC/C(C1=CC=CC=C1)=C/Cl.[H]Cl
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
Biological target:
MDL-72274 HCl is selective and potent inhibitors of SSAO for treatment of Parkinson diseases.
In vitro activity:
These halogen-containing compounds were irreversible inhibitors of SSAO after preincubation with aorta homogenates; kinetic evidence for an initial competitive, reversible interaction (Ki around 0.4-0.6 microM) was found with two compounds (MDL 72145 and 72274). Of particular interest in this study is the finding that (E)-2-phenyl-3-chloroallylamine (MDL 72274) is highly selective as an inhibitor of SSAO, compared with MAO-A or B activities.
Reference: Biochem Pharmacol. 1987 Sep 1;36(17):2847-53. https://pubmed.ncbi.nlm.nih.gov/3632710/
In vivo activity:
Histamine oxidation by rat white adipocytes is enhanced by elevated pH and by the presence of bicarbonate ions. The specific semicarbazide-sensitive amine oxidase (SSAO) inhibitors MDL 72274 and B24 inhibit the oxidation of both histamine and benzylamine by the adipocyte preparation.
Reference: Inflamm Res. 1997 Apr;46(4):125-31. https://pubmed.ncbi.nlm.nih.gov/9137990/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
204.09
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.
| 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 |
Formulation protocol:
Lyles GA, Marshall CM, McDonald IA, Bey P, Palfreyman MG. Inhibition of rat aorta semicarbazide-sensitive amine oxidase by 2-phenyl-3-haloallylamines and related compounds. Biochem Pharmacol. 1987 Sep 1;36(17):2847-53. doi: 10.1016/0006-2952(87)90275-9. PMID: 3632710.
2. Raimondi L, Banchelli G, Ignesti G, Pirisino R, Conforti L. The histaminase activity of rat white adipocytes. Inflamm Res. 1997 Apr;46(4):125-31. doi: 10.1007/s000110050535. PMID: 9137990.
In vitro protocol:
Lyles GA, Marshall CM, McDonald IA, Bey P, Palfreyman MG. Inhibition of rat aorta semicarbazide-sensitive amine oxidase by 2-phenyl-3-haloallylamines and related compounds. Biochem Pharmacol. 1987 Sep 1;36(17):2847-53. doi: 10.1016/0006-2952(87)90275-9. PMID: 3632710.
In vivo protocol:
Raimondi L, Banchelli G, Ignesti G, Pirisino R, Conforti L. The histaminase activity of rat white adipocytes. Inflamm Res. 1997 Apr;46(4):125-31. doi: 10.1007/s000110050535. PMID: 9137990.
1: Conklin DJ, Bhatnagar A, Cowley HR, Johnson GH, Wiechmann RJ, Sayre LM, Trent MB, Boor PJ. Acrolein generation stimulates hypercontraction in isolated human blood vessels. Toxicol Appl Pharmacol. 2006 Dec 15;217(3):277-88. Epub 2006 Sep 29. PubMed PMID: 17095030; PubMed Central PMCID: PMC3487162.
2: Holt A, Todd KG, Baker GB. The effects of chronic administration of inhibitors of flavin and quinone amine oxidases on imidazoline I(1) receptor density in rat whole brain. Ann N Y Acad Sci. 2003 Dec;1009:309-22. PubMed PMID: 15028605.
3: Langford SD, Trent MB, Boor PJ. Semicarbazide-sensitive amine oxidase and extracellular matrix deposition by smooth-muscle cells. Cardiovasc Toxicol. 2002;2(2):141-50. PubMed PMID: 12271157.
4: Pirisino R, Ghelardini C, Banchelli G, Galeotti N, Raimondi L. Methylamine and benzylamine induced hypophagia in mice: modulation by semicarbazide-sensitive benzylamine oxidase inhibitors and aODN towards Kv1.1 channels. Br J Pharmacol. 2001 Oct;134(4):880-6. PubMed PMID: 11606329; PubMed Central PMCID: PMC1573009.
5: Banchelli G, Ghelardini C, Raimondi L, Galeotti N, Pirisino R. Selective inhibition of amine oxidases differently potentiate the hypophagic effect of benzylamine in mice. Eur J Pharmacol. 2001 Feb 9;413(1):91-9. PubMed PMID: 11173067.
6: Langford SD, Trent MB, Balakumaran A, Boor PJ. Developmental vasculotoxicity associated with inhibition of semicarbazide-sensitive amine oxidase. Toxicol Appl Pharmacol. 1999 Mar 15;155(3):237-44. PubMed PMID: 10079209.
7: Raimondi L, Banchelli G, Ignesti G, Pirisino R, Conforti L. The histaminase activity of rat white adipocytes. Inflamm Res. 1997 Apr;46(4):125-31. PubMed PMID: 9137990.
8: Palfreyman MG, McDonald IA, Bey P, Danzin C, Zreika M, Cremer G. Haloallylamine inhibitors of MAO and SSAO and their therapeutic potential. J Neural Transm Suppl. 1994;41:407-14. PubMed PMID: 7931257.
9: Lyles GA, Marshall CM, McDonald IA, Bey P, Palfreyman MG. Inhibition of rat aorta semicarbazide-sensitive amine oxidase by 2-phenyl-3-haloallylamines and related compounds. Biochem Pharmacol. 1987 Sep 1;36(17):2847-53. PubMed PMID: 3632710.
