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- CAS:
- 57-42-1
- MF:
- C15H21NO2
- MW:
- 247.33
Properties
- Melting point::
- 270°C
- Boiling point::
- 390.37°C (rough estimate)
- Density :
- 1.0267 (rough estimate)
- refractive index :
- 1.5130 (estimate)
- Flash point::
- 11 °C
- storage temp. :
- −20°C
- pka:
- pKa 8.7 (Uncertain)
- Water Solubility :
- 6.55g/L(25 ºC)
- BCS Class:
- 1
SecurityInformation
- Symbol(GHS) :
-
GHS02,GHS06,GHS08
- Signal word :
- Danger
- Hazard statements :
- H225-H301+H311+H331-H370
- Precautionary statements :
- P210-P260-P280-P301+P310-P311
- Hazard Codes :
- F,T
- Risk Statements :
- 11-23/24/25-39/23/24/25
- Safety Statements :
- 7-16-36/37-45
- RIDADR :
- UN 1230 3/PG 2
- WGK Germany :
- 1
- Toxicity:
- A narcotic analgesic used for moderate to severe pain and during obstetrical anesthesia. Its oral LD50 in rats is 170 mg/kg. It has multiple actions qualitatively similar to those of morphine, and therapy is similar to that for morphine. Advantages over morphine concerning efficacy and reduced risk of addiction were largely illusory. This, and potential drug interactions, have resulted in a dramatic reduction in use.
- Use:
- Meperidine (Demerol) was discovered in 1939 during a serendipitous screening of compounds being studied for antispasmodic activity. Mice given meperidine were noted to carry their tails in an erect position (the Straub tail reaction), which was indicative of narcotic analgesia. This led to the study of meperidine and derivatives as analgesic agents. Meperidine was found to have low potency at the receptor compared with morphine (0.2%) but much higher penetration into the brain resulting in a compound with about 10% of the potency of morphine.Structural changes that increase the potency of meperidine include the introduction of an mhydroxyl on the phenyl ring, substituting the methyl on the N for a phenylethyl or a p-aminophenylethyl. Replacing the N-methyl with an N-allyl or N-cyclopropylmethyl group does not generate an antagonist, unlike the similar substitution of the morphine congeners. Meperidine quickly penetrates the blood-brain barrier and thus has a quick onset of activity and a high abuse potential.
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