| Identification | Back Directory | [Name]
MEPERIDINE HYDROCHLORIDE | [CAS]
50-13-5 | [Synonyms]
s140
wy554
algil
dolin
lidol
mepadin
dolosal
endolat
dolaren
petidin
Mialgin
Antiduol
dolargan
dolantol
dispadol
dolantal
dolvanol
mefedina
mephedine
operidine
pentantin
antidurol
Dolestine
piridosal
spasmedal
dolopethin
centralgin
dolcontral
pantalgine
doloneurine
spasmodolin
synelaudine
sauteralgyl
chlorbycyclen
alodan(gerot)
chlorbicyclene
MEPERIDINE HCL
pethidinechloride
demerolhydrochloride
dolantinhydrochloride
petantinhydrochloride
PETHIDINE HYDROCHLORIDE
MEPERIDINE HYDROCHLORIDE
isonipecainehydrochloride
MEPERIDINEHYDROCHLORIDE,USP
Meperidine (hydrochloride) (CRM)
Meperidine hydrochloride solution
Meperidine solution hydrochloride
Meperidine Hydrochloride (CII), USP
Meperidine Hydrochloride CII (200 mg)
Meperidine Hydrochloride CII (1383001)
MEPERIDINE HYDROCHLORIDE--DEA SCHEDULE &
meperidine hydrochloride*methanol solution
ethyl-1-methyl-4-phenylisonipecotatehydrochloride
n-methyl-4-phenyl-4-carbethoxypiperidinehydrochloride
1-methyl-4-carbethoxy-4-phenylpiperidinehydrochloride
1-methyl-4-phenyl-4-carboethoxypiperidinehydrochloride
1-methyl-4-phenylisonipecoticacidethylesterhydrochloride
ethyl1-methyl-4-phenylpiperidyl-4-carboxylatehydrochloride
isonipecoticacid,1-methyl-4-phenyl-,ethylester,hydrochloride
4-piperidinecarboxylicacid,1-methyl-4-phenyl-,ethylester,hydrochloride
1-METHYL-4-PHENYLPIPERIDINE-4-CARBOXYLIC ACID ETHYL ESTER HYDROCHLORIDE
Pethidine hydrochloride, 1-Methyl-4-phenylpiperidine-4-carboxylic acid ethyl ester hydrochloride | [EINECS(EC#)]
200-013-3 | [Molecular Formula]
C15H22ClNO2 | [MDL Number]
MFCD00058210 | [MOL File]
50-13-5.mol | [Molecular Weight]
283.79 |
| Chemical Properties | Back Directory | [Definition]
An addictive drug,
use by prescription only. | [Appearance]
White or almost white, crystalline powder. | [Melting point ]
186-189° | [Boiling point ]
282°C (rough estimate) | [density ]
1.0858 (rough estimate) | [refractive index ]
1.5200 (estimate) | [Fp ]
11 °C | [storage temp. ]
2-8°C | [solubility ]
Very soluble in water, freely soluble in alcohol. | [form ]
A crystalline solid | [CAS DataBase Reference]
50-13-5 |
| Hazard Information | Back Directory | [Chemical Properties]
White or almost white, crystalline powder. | [Uses]
Analgesic; sedative; anesthetic.
Controlled substance (opiate). | [Brand name]
Demerol (Hospira); Demerol (Sanofi
Aventis). | [Originator]
Dolosal,Specia,France,1943 | [Manufacturing Process]
80 parts of finely pulverized sodium amide are added in portions each of about ? of the entire quantity, while stirring and cooling in a suitable manner, to a mixture of 756 parts of methyl-di(β-chloroethyl)-amine (prepared from di-ethanol-methylamine by means of thionyl chloride), 117 parts of benzyl cyanide and 600 parts of toluene. The reaction sets in at once at room temperature. The temperature is maintained between 30° and 40°C; when self-heating no longer occurs a further portion of the sodium amide is introduced. During the reaction heat is liberated and gaseous ammonia escapes.
The mixture is then slowly heated to the boiling point of toluene and kept
boiling for one hour under reflux. After the mixture has been allowed to cool
the sodium chloride which precipitates is separated by extraction with water.
The solution of toluene is then extracted with dilute hydrochloric acid. From
the hydrochloric acid extract the basic substance is separated in the form of
an oil by means of caustic soda solution and is introduced into ether. The
ethereal solution is dried with the aid of potassium carbonate and then
distilled.
Under a pressure of 4.5 ml the 1-methyl-4-phenyl-piperidine-4-carboxylic acid
nitrile passes over at a temperature of about 148°C in the form of a colorless
oil; under a pressure of 6 ml it passes over at about 158°C. After having been
allowed to cool the distillate solidifies completely to form a crystalline mass.
Its solidification point is at 53°C; the yield amounts to about 135 parts, that
is, about 2/3 of the theoretical yield. When recrystallized from isopropyl
alcohol the hydrochloride of the nitrile forms colorless crystals, readily soluble
in water and melting at 221° to 222°C.
The nitrile may best be saponified with methyl alcoholic potash while heating
to 190° to 200°C with application of pressure. After the methyl alcohol has
evaporated the salt is introduced into water and by the addition of dilute
mineral acid until the alkaline reaction to phenolphthalein has just
disappeared, the amphoteric 1-methyl-4-phenyl-piperidine-4-carboxylic acid is
precipitated while hot in the form of a colorless, coarsely crystalline powder.
When dried on the water bath the acid still contains 1 mol of crystal water
which is lost only at a raised temperature. The acid melts at 299°C. Reaction
with ethanol yields the ester melting at 30°C and subsequent reaction with
HCl gives the hydrochloride melting at 187° to 188°C. | [Therapeutic Function]
Narcotic analgesic | [Biochem/physiol Actions]
Phenylpiperidine analgesic; sedative; μ opioid receptor agonist with greater κ opioid receptor agonist activity than morphine. | [Clinical Use]
Meperidine is a μ agonist with approximately one-tenth the potency of morphine after intramuscular
dose. Meperidine produces the analgesia, respiratory depression, and euphoria caused by other μ
opioid agonists, but it causes less constipation and does not inhibit cough. When given orally,
meperidine has 40 to 60% bioavailability because of significant first-pass metabolism. Because of
the limited bioavailability, it is one-third as potent after an oral dose compared to a parenteral
dose.
Meperidine has received extensive use in obstetrics because of its rapid onset and short duration
of action. When it is given intravenously in small (25-mg) doses during delivery, the respiratory
depression in the newborn child is minimized. Meperidine is used as an analgesic
in a variety of nonobstetric anesthetic procedures. Meperidine is extensively metabolized in the
liver, with only 5% of the drug being excreted unchanged. Prolonged dosage of meperidine may
cause an accumulation of the metabolite normeperidine. Normeperidine has only weak analgesic activity, but it causes CNS excitation and can
initiate grand mal seizures. It is recommended that meperidine be discontinued in any patient who
exhibits signs of CNS excitation.
Meperidine has a strong adverse reaction when given to patients receiving a monoamine oxidase
inhibitor. This drug interaction has been seen recently in patients with Parkinson's disease taking
the monoamine oxidase–selective inhibitor selegiline (Eldepryl).
The elimination half-life of meperidine is 3 to 4 hours, and it can double in patients with liver
disease. Acidification of the urine will cause enhanced clearance of meperidine, but there is a
lesser effect on the clearance of the toxic metabolite normeperidine. | [Veterinary Drugs and Treatments]
Although no product is licensed in the United States for veterinary
use, this agent has been used as an analgesic in several different species.
It has been used as sedative/analgesic in small animals for both
post-operative pain and for medical conditions such as acute pancreatitis
and thermal burns, but usually other opiates are preferred
as the drug has a short analgesic duration of activity and can cause
significant histamine release. It is occasionally used in equine medicine
in the treatment of colic and in other large animal species for
pain control. | [Drug interactions]
Potentially hazardous interactions with other drugs
Analgesics: possible opioid withdrawal with
buprenorphine and pentazocine.
Anti-arrhythmics: delayed absorption of mexiletine.
Antidepressants: possible CNS excitation or
depression with MAOIs and moclobemide -
avoid; possibly increased serotonergic effects with
duloxetine; increased sedative effects with tricyclics.
Antiepileptics: possible increased risk of pethidine
toxicity with fosphenytoin and phenytoin.
Antihistamines: increased sedative effects with
sedating antihistamines.
Antipsychotics: enhanced sedative and hypotensive
effect.
Antivirals: concentration reduced by ritonavir but
concentration of toxic pethidine metabolite increased
- avoid.
Dopaminergics: risk of CNS toxicity with rasagiline
- avoid; hyperpyrexia and CNS toxicity reported
with selegiline - avoid.
Nalmefene: avoid concomitant use.
Sodium oxybate: enhanced effect of sodium oxybate
- avoid. | [Metabolism]
Pethidine is metabolised in the liver by hydrolysis to
pethidinic acid or by demethylation to norpethidine
(active metabolite) and hydrolysis to norpethidinic
acid, followed by conjugation with glucuronic acid.
Norpethidine is pharmacologically active and its
accumulation may result in toxicity. Pethidine has a
half-life of about 3-6 hours; norpethidine is eliminated
more slowly, with a half-life reported to be up to about 20
hours. |
| Safety Data | Back Directory | [Hazard Codes ]
T,F | [Risk Statements ]
25-39/23/24/25-23/24/25-11 | [Safety Statements ]
26-36/37/39-45-36/37-16-7 | [RIDADR ]
1544 | [WGK Germany ]
3 | [RTECS ]
NS5950000 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
2933330000 | [Safety Profile]
Poison by ingestion,
subcutaneous, intravenous, and
intraperitoneal routes. Moderately toxic by
parenteral route. Experimental teratogenic
effects. Mutation data reported. An
analgesic. When heated to decomposition it
emits very toxic fumes of HCl and NOx. | [Toxicity]
LD50 orally in rats: 170 mg/kg (Barlow, Lewis) |
|