Procyclidine: Difference between revisions

{{Short description|Group of stereoisomers}}

{{distinguish|Phencyclidine}}

{{Drugbox

| verifiedrevid = 267631655

| image = Procyclidine-hydrochloride-2D-skeletal.png

<!--Clinical data-->

| tradename =

| Drugs.com = {{drugs.com|monograph|procyclidine-hydrochloride}}

| MedlinePlus = a605037

| pregnancy_category =

| legal_status =

| routes_of_administration = [[Oral administration|By mouth]], [[intramuscular|im]], [[intravenous|iv]]

<!--Pharmacokinetic data-->

| bioavailability =

| protein_bound = ~100%-albumin

| metabolism =

| elimination_half-life = ~12 h

| excretion =

<!--Identifiers-->

| CAS_number = 77-37-2

| ATC_prefix = N04

| DrugBank = DB00387

| ChemSpiderID = 4750

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = C6QE1Q1TKR

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1761

<!--Chemical data-->

'''Procyclidine''' is an [[anticholinergic]] [[medication|drug]] principally used for the treatment of drug-induced [[parkinsonism]], [[akathisia]] and acute [[dystonia]], [[Parkinson's disease]], and [[idiopathic]] or secondary [[dystonia]].

== Uses ==

It is used in patients with [[parkinsonism]] and [[akathisia]], and to reduce the side effects of [[antipsychotic]] treatment given for [[schizophrenia]]. Procyclidine is also a second-line drug for the treatment of [[Parkinson's disease]]. It improves [[tremor]] but not rigidity or [[bradykinesia]].

== 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.

==Synthesis==

[[File:Procyclidine synthesis.png|thumb|center|500px|Procyclidine synthesis:<ref>{{Cite patent|country=DE|number=1084734|pubdate=1960-07-07|title=Verfahren zur Herstellung von tertiäeren Aminoalkoholen [Process for the preparation of tertiary amino alcohols]|assign1=VEB Fahlberg-List Chemische und Pharmazeutische Fabriken|inventor1-last=Jassmann|inventor1-first=Edgar|inventor2-last=Pfanz|inventor2-first=Hermann}}</ref> {{US patent|2826590}}]]

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.

[[File:Procyclidine synthesis2.png|thumb|center|400px|Procyclidine synthesis 2<ref>{{cite journal| vauthors = Adamson DW, Barrett PA, Wilkinson S |title=11. Aminoalkyl tertiary carbinols and derived products. Part IV. Spasmolytics. Phenyl- and cyclohexylphenyl-carbinols|journal=Journal of the Chemical Society (Resumed)|year=1951|pages=52|doi=10.1039/jr9510000052}}</ref>]]

In an interesting variation, the ketone is first reacted with phenylmagnesium bromide. [[Catalytic hydrogenation]] of the [[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.

<ref>{{cite web |url=https://bnf.nice.org.uk/drug/procyclidine-hydrochloride.html |title=Procyclidine Hydrochloride |publisher=National Institute for Health and Care Excellence | access-date=2020-07-06}}</ref>

== See also ==

*[[Benzatropine]]

*[[Biperiden]]

*[[Cycrimine]]

== References ==

{{Reflist}}

== Further reading ==

* {{cite book | title=British National Formulary | edition=45 |date=March 2003| title-link=British National Formulary }}

{{Antiparkinson}}

{{Hallucinogens}}

{{Muscarinic acetylcholine receptor modulators}}

[[Category:Tertiary alcohols]]

[[Category:Chlorides]]

[[Category:1-Pyrrolidinyl compounds]]

[[Category:Cyclohexyl compounds]]