Compound: meperidine
SMILES: O=C(OCC)C1(c2ccccc2)CCN(C)CC1
InChIKey: XADCESSVHJOZHK-UHFFFAOYSA-N
Synonyms: meperidine, Pethidine, Isonipecaine, Pethidineter, Meperidol, Pethanol, Pethidin, Phetidine, Nemerol, Pipersal, Ethyl 1-methyl-4-phenylpiperidine-4-carboxylate, Petydyna, 57-42-1, Petidina, Pethidinum, Ethyl 1-methyl-4-phenylisonipecotate, Renaudin, Pethidine DBL, 4-Piperidinecarboxylic acid, 1-methyl-4-phenyl-, ethyl ester, Dolsin, Lydol, Methyl phenylpiperidine carbonic acid ethyl ester, Isonipecotic acid, 1-methyl-4-phenyl-, ethyl ester, N-Methyl-4-phenyl-4-carbethoxypiperidine, 1-Methyl-4-phenylpiperidine-4-carboxylic acid ethyl ester, 1-Methyl-4-phenylisonipecotic acid, ethyl ester, IDS-NP-001, 1-Methyl-4-phenyl-4-piperidinecarboxylic acid ethyl ester, CHEBI:6754, 9E338QE28F, 1-Methyl-4-phenyl-piperidin-4-carbon-saeure-aethylester, DTXSID9023253, Isonipecain, Operidine EPJ I, RefChem:5997, DTXCID403253, N02AB02, 200-329-1, Dolcontral, Dolosal, Demerol, HSDB 3116, Pethidine (INN), CHEMBL607, Pethidine [INN], meperidina, Meperidine-d5, Petydyna [Polish], Demarol, Piperosal, Pethidinum [INN-Latin], Petidina [INN-Spanish], 1-Methyl-4-phenyl-piperidine-4-carboxylic acid ethyl ester, Pethidine [INN:BAN], EINECS 200-329-1, UNII-9E338QE28F, DEA No. 9230, 1-Methyl-4-phenyl-piperidin-4-carbon-saeure-aethylester [German], Lidol (Salt/Mix), Lydol (Salt/Mix), Dolsin (Salt/Mix), Pethidine impurity 6, Pethidine impurity 7, Dolaren (Salt/Mix), Dolosal (Salt/Mix), 53484-75-6, Dispadol (Salt/Mix), Dolantin (Salt/Mix), Petantin (Salt/Mix), Operidine (Salt/Mix), Piridosal (Salt/Mix), Pethidine Impurity 14, 4-Carbethoxy-1-methyl-4-phenylpiperidine, Centralgin (Salt/Mix), Dolcontral (Salt/Mix), MEPERIDINE [MI], MEPERIDINE [HSDB], MEPERIDINE [VANDF], Epitope ID:549276, 1-methyl-4-phenylisonipecotic acid ethyl ester, PETHIDINE [WHO-DD], SCHEMBL25431, DivK1c_000983, GTPL7221, KBio1_000983, NINDS_000983, YIsonipecotic acid, 1-methyl-4-phenyl-, ethyl ester (8CI), BDBM50026752, 50-13-5(HCl), DB00454, IDI1_000983, DB-053051, NS00009544, C07128, D08343, Pethidine (Meperidine) 0.1 mg/ml in Methanol, Pethidine (Meperidine) 1.0 mg/ml in Methanol, Q55434, 4-Ethoxycarbonyl-1-methyl-4-phenyl-piperidinium, Ethyl 1-methyl-4-phenyl-4-piperidinecarboxylate, L000908, SR-01000944492, SR-01000944492-1, 1-Methyl-4-phenyl-piperidine-4-carboxylic acid ethyl ester(Meperidine)
Theoretical properties:
molecular_formula: C15H21NO2
molecular_weight: 247.33 g/mol
exact_mass: 247.157228913 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 4
heavy_atom_count: 18
topological_polar_surface_area: 29.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Solid
color: Solid
Descriptions:
{"pubchem": "Pethidine is a piperidinecarboxylate ester that is piperidine which is substituted by a methyl group at position 1 and by phenyl and ethoxycarbonyl groups at position 4. It is an analgesic which is used for the treatment of moderate to severe pain, including postoperative pain and labour pain. It has a role as an opioid analgesic, an antispasmodic drug, a mu-opioid receptor agonist and a kappa-opioid receptor agonist. It is an ethyl ester, a piperidinecarboxylate ester and a tertiary amino compound. It is a conjugate base of a pethidine(1+).", "chebi": "A piperidinecarboxylate ester that is piperidine which is substituted by a methyl group at position 1 and by phenyl and ethoxycarbonyl groups at position 4. It is an analgesic which is used for the treatment of moderate to severe pain, including postoperative pain and labour pain.", "chembl": "MEPERIDINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a fully synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Otto Eisleb, its analgesic properties were first recognized by Otto Schaumann while working for IG Farben, in Germany. Pethidine is the prototype of a large family of analgesics including the pethidine 4-phenylpiperidines (e.g., piminodine, anileridine), the prodines (e.g., alphaprodine, MPPP), bemidones (e.g., ketobemidone), and others more distant, including diphenoxylate and analogues.\nPethidine is indicated for the treatment of moderate to severe pain, and is delivered as a hydrochloride salt in tablets, as a syrup, or by intramuscular, subcutaneous, or intravenous injection. For much of the 20th century, pethidine was the opioid of choice for many physicians; in 1975, 60% of doctors prescribed it for acute pain and 22% for chronic severe pain.\nIt was patented in 1937 and approved for medical use in 1943. Compared with morphine, pethidine was considered to be safer, carry a lower risk of addiction, and to be superior in treating the pain associated with biliary spasm or renal colic due to its assumed anticholinergic effects. These were later discovered to be inaccurate assumptions, as it carries an equal risk of addiction and possesses no advantageous effects on biliary spasm or renal colic compared to other opioids. Due to the neurotoxicity of its metabolite, norpethidine, it is more toxic than other opioids\u2014especially during long-term use. The norpethidine metabolite was found to have serotonergic effects, so pethidine could, unlike most opioids, increase the risk of triggering serotonin syndrome."}