CAS 18903-01-0 1-Cinnamylpiperazine (HCID 726896)

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Basic information

CAS: 18903-01-0
Standard SMILES: C(=C\c1ccccc1)/CN1CCNCC1
InChIKey: WGEIOMTZIIOUMA-QPJJXVBHSA-N
Molecular formula: C13H18N2
Average molar mass: 202.3 g/mol
Monoisotopic mass: 202.14699858

Names & identifiers

Preferred name: 1-Cinnamylpiperazine
IUPAC: 1-[(E)-3-phenylprop-2-enyl]piperazine
English name: trans-1-Cinnamylpiperazine
Molecular formula: C13H18N2
Molecular weight: 202.3

Names & synonyms

1-Cinnamylpiperazine18903-01-0EINECS 242-652-0RefChem:431512242-652-0trans-1-Cinnamylpiperazine87179-40-61-(3-phenyl-2-propenyl)piperazine(E)-1-Cinnamylpiperazine1-(Cinnamyl)piperazine1-(3-phenylprop-2-en-1-yl)piperazine1-((E)-3-Phenylallyl)piperazine

Show more names

TIMTEC-BB SBB000411Flunarizine Impurity 9LABOTEST-BB LT00233225trans-1-Ciamylpiperazine1-TRANS-CINNAMYL PIPERAZINE1-(3-PHENYL-ALLYL)-PIPERAZINE

N-CinnamylpiperazineMFCD000632511-[(2E)-3-phenylprop-2-en-1-yl]piperazine1-[(E)-3-phenylprop-2-enyl]piperazineSCHEMBL1151817Piperazine, 1-(3-phenyl-2-propen-1-yl)-cinnamylpiperazinePiperazine, 1-[(2E)-3-phenyl-2-propen-1-yl]-

Database identifiers

CAS: 18903-01-0、87179-40-6
PubChem CID: 726896
DTXSID: DTXSID501035300
ChEMBL: CHEMBL503140
EC Number: 242-652-0、673-639-1
Nikkaji: J29.025D

Properties

Computed structural properties

XLogP: 1.7
Topological polar surface area: 15.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 15
Formal charge: 0
Complexity: 189

Physicochemical properties

Melting point: 39 · 39-44 °C(lit.)
Boiling point: 129 °C1 · 129 °C1 mm Hg(lit.)
Density: 0.989 g/mL · 0.989 g/mL at 25 °C(lit.)
refractive index: 1.574 · 1.574-1.576
Flash point: 230 °F · >230 °F
storage temp.: Refrigerator, under inert atmosphere
solubility: Chloroform (Sparingly), Methanol (Slightly)
form: Solid
pka: 9.17 · 9.17±0.10(Predicted)
color: Pale Yellow
BRN: 608984 · 608984
InChI: InChI=1S/C13H18N2/c1-2-5-13(6-3-1)7-4-10-15-11-8-14-9-12-15/h1-7,14H,8-12H2/b7-4+
InChIKey: WGEIOMTZIIOUMA-QPJJXVBHSA-N
SMILES: N1(C/C=C/C2=CC=CC=C2)CCNCC1
CAS DataBase Reference: 87179 · 87179-40-6(CAS DataBase Reference)

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

Hazard information

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (100%)

Safety data

wgk: 3
hs_code: 29335995
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36-37/39
Hazard statements: H315-H319-H335
Precautionary statements: P261-P305+P351+P338-P280a-P304+P340-P405-P501a

Chemistry & industry

Pharmacology

Metabolism/Metabolites1-Cinnamylpiperazine is a known human metabolite of cinnarizine.

Applications · 5 items

Descriptiontrans-1-Cinnamylpiperazine is a piperazine derivative. It was used as a test compound to investigate the in vitro efficacy as an antiprotozoal against Philasterides dicentrarchi. It may be used to synthesize Incentrom A derivatives.

Usestrans-1-Cinnamylpiperazine is used in the synthesis of bile acid piperazinyl derivatives which display pro-apoptotic properties on carcinoma human cell lines.

Usestrans-1-Cinnamylpiperazine was used as a test compound to investigate the in vitro efficacy as an antiprotozoal against Philasterides dicentrarchi. It may be used to synthesize Incentrom A derivatives.

General Descriptiontrans-1-Cinnamylpiperazine is a piperazine derivative.

General Descriptiontrans-1-Cinnamylpiperazine is an important organic synthetic reagent for the preparation of opioid tripeptides hybridised with trans-1-Cinnamylpiperazine, which exhibits low haematotoxicity and good cancer cell growth as an inhibitor of pancreatic cancer cell proliferation in two- and three-dimensional in vitro models Inhibition. It was also used in the preparation of the anticonvulsant active substance cinnamylpiperazine derivatives.