Procyclidine

Source: Wikipedia, the free encyclopedia.
Not to be confused with Phencyclidine.
Procyclidine
iv
ATC code
Pharmacokinetic data
Protein binding~100%-albumin
Elimination half-life~12 h
Identifiers
  • 1-cyclohexyl-1-phenyl-3-pyrrolidin-1-yl-propan-1-ol hydrochloride
ECHA InfoCard
100.000.931 Edit this at Wikidata
Chemical and physical data
FormulaC19H30ClNO
Molar mass323.90 g·mol−1
  (verify)

Procyclidine is an

idiopathic or secondary dystonia
.

Uses

It is used in patients with

bradykinesia
.

Procyclidine is also sometimes used for the treatment of dystonia (but not tardive dyskinesia), a rare disorder that causes abnormal muscle contraction, resulting in twisting postures of limbs, trunk, or face.

Overdose

Signs of procyclidine overdose are those of an anticholinergic and include confusion, agitation and sleeplessness that can last up to or more than 24 hours. Pupils become dilated and unreactive to light. Tachycardia (fast heart beat), as well as auditory and visual hallucinations have also been reported.

Other known symptoms of overdose are: clumsiness or unsteadiness, being severely drowsy, having a severely dry mouth, nose, or throat, having an altered mood or other mental changes, seizures, being short of breath or having troubled breathing, a dry and warm, flushed skin.

A suspected overdose with severe life-threatening symptoms should immediately be brought to medical attention, where reversal can be attempted with physostigmine administered intravenously or subcutaneously.

Synthesis

Procyclidine synthesis:[1] U.S. patent 2,826,590

Procyclidine, 1-cyclohexyl-1-phenyl-3-pyrrolidinopropan-1-ol, is synthesized in exactly the same manner as was seen for trihexyphenidyl, except this time the linear synthesis begins with the preparation of 3-(1-pyrrolidino)propiophenone.

Procyclidine synthesis 2[2]

In an interesting variation, the ketone is first reacted with phenylmagnesium bromide.

carbinol
thus obtained can be stopped after the reduction of only one aromatic ring.

Side Effects

Side effects include nausea, constipation, urinary retention, blurred vision, anxiety, cognitive impairment, confusion, dizziness, gingivitis, hallucination, memory loss, rash and vomiting. [3]

See also

References

  1. ^ DE 1084734, Jassmann, Edgar & Pfanz, Hermann, "Verfahren zur Herstellung von tertiäeren Aminoalkoholen [Process for the preparation of tertiary amino alcohols]", published 1960-07-07, assigned to VEB Fahlberg-List Chemische und Pharmazeutische Fabriken 
  2. doi:10.1039/jr9510000052
    .
  3. ^ "Procyclidine Hydrochloride". National Institute for Health and Care Excellence. Retrieved 2020-07-06.

Further reading

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