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MedKoo Cat#: 318909 | Name: Benzhexol HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Benzhexol, also known as Trihexyphenidyl, is an antiparkinsonian agent of the antimuscarinic class. It has been in clinical usage for decades.

Chemical Structure

Benzhexol HCl
Benzhexol HCl
CAS#52-49-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 318909

Name: Benzhexol HCl

CAS#: 52-49-3 (HCl)

Chemical Formula: C20H32ClNO

Exact Mass: 301.2406

Molecular Weight: 337.93

Elemental Analysis: C, 71.09; H, 9.55; Cl, 10.49; N, 4.14; O, 4.73

Price and Availability

Size Price Availability Quantity
500mg USD 110.00 Ready to ship
1g USD 180.00 Ready to ship
2g USD 300.00 Ready to ship
5g USD 650.00 2 weeks
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Related CAS #
52-49-3 (HCl) 144-11-6 (free base)
Synonym
Trihexyphenidyl, Benzhexol, Trihex, Artane, Apo-Trihex, Parkin, Pacitane; Benzhexol HCl; Benzhexol hydrochloride
IUPAC/Chemical Name
1-cyclohexyl-1-phenyl-3-piperidin-1-ylpropan-1-ol hydrochloride
InChi Key
QDWJJTJNXAKQKD-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H31NO.ClH/c22-20(18-10-4-1-5-11-18,19-12-6-2-7-13-19)14-17-21-15-8-3-9-16-21;/h1,4-5,10-11,19,22H,2-3,6-9,12-17H2;1H
SMILES Code
OC(C1=CC=CC=C1)(C2CCCCC2)CCN3CCCCC3.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#T9C03I26
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Trihexyphenidyl hydrochloride is an antiparkinsonian agent of the antimuscarinic class, binds to the M1 muscarinic receptor.
In vitro activity:
The protective effect of Trihexyphenidyl (THY) on Aβ(25-35)-induced cytotoxicity in cultured rat pheochromocytoma (PC12) cells was investigatecd. In this report, the cell survival was measured by MTT assay, the enzyme activity of superoxide dismutase (SOD) and glutathione peroxidase (GSH-PX), the contents of lipid peroxidation products malondialdehyde (MDA) and ROS in the cells were determined. Acridine orange (AO) was used to observe the morphological characteristic of apoptotic cells. Mitochondrial membrane potential in PC12 cells were monitored by fluorospectrophotometer combining with Rh123. As a cell permeable fluorescent probe, Fura-2/AM was employed to detect intracellular [Ca(2+)]. The results showed that after incubation with Aβ(25-35) (10 μM) for 24 h, there were decreased changes in cell viability, SOD, and GSH-PX activity as well as mitochondrial membrane potential, in contrast, the levels of [Ca(2+)](i), ROS, and MDA were increased, THY significantly attenuated all the changes induced by Aβ(25-35), indicating that THY exhibited protective effect against Aβ(25-35)-induced cytotoxicity, which may represent the cellular mechanisms of the action. Reference: Clin Exp Med. 2010 Dec;10(4):237-43. https://dx.doi.org/10.1007/s10238-010-0090-9
In vivo activity:
To test the DA-enhancing effects of Benzhexol (Trihexyphenidyl, THP) in vivo, microdialysis was conducted in awake, behaving mice. THP was reverse dialyzed and extracellular DA was measured both pre- and post- treatment (Fig 3A). Extracellular DA was significantly reduced at baseline in Dyt1 mice relative to controls (Tor1a+/+, 3.07 ± 0.434 ng/mL, Tor1a+/ΔE, 1.88 ± 0.205 ng/mL; Student’s t test, p<0.05), consistent with previous results. THP significantly increased extracellular DA in both control and Dyt1 mice (two-way repeated measures ANOVA, main effect of treatment, F1,14 = 38.02, p<0.0001). In fact, THP increased extracellular DA in Dyt1 mice to normal WT concentrations (Tukey’s post-hoc, p>0.05). Additionally, extracellular DA was measured using microdialysis after a single peripheral administration of THP (20 mg/kg i.p.). Previous studies demonstrated that this dose reduces the severity of the dystonia in a mouse model of DOPA-responsive dystonia, but does not reduce locomotor activity. Peripherally administered THP significantly increased extracellular DA (Fig 3B); (two-way repeated measures ANOVA, main effect of treatment, F1,16 = 7.003, p<0.05). Reference: Neurobiol Dis. 2019 May;125:115-122. doi: 10.1016/j.nbd.2019.01.012. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30707939/
Solvent mg/mL mM
Solubility
DMSO 20.0 59.18
DMSO 20.0 59.18
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 337.93 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Liu ZZ, Ji BS. The protective effect of trihexyphenidyl on the beta-amyloid peptide (25-35)-induced cytotoxicity in PC12 cells. Clin Exp Med. 2010 Dec;10(4):237-43. doi: 10.1007/s10238-010-0090-9. Epub 2010 Jan 26. PMID: 20101432.
In vivo protocol:
1. Downs AM, Fan X, Donsante C, Jinnah HA, Hess EJ. Trihexyphenidyl rescues the deficit in dopamine neurotransmission in a mouse model of DYT1 dystonia. Neurobiol Dis. 2019 May;125:115-122. doi: 10.1016/j.nbd.2019.01.012. Epub 2019 Jan 30. PMID: 30707939; PMCID: PMC6863078.
1: Lee CP, Chen PJ, Chang CM. Heat stroke during treatment with olanzapine, trihexyphenidyl, and trazodone in a patient with schizophrenia. Acta Neuropsychiatr. 2015 Dec;27(6):380-5. doi: 10.1017/neu.2015.29. PubMed PMID: 26503496. 2: Begbie F, Walker G, Kubba H, Sabharwal A. Acute colonic pseudo-obstruction in a child taking trihexyphenidyl for drooling: Prescribers beware. Int J Pediatr Otorhinolaryngol. 2015 Jun;79(6):932-4. doi: 10.1016/j.ijporl.2015.03.027. Epub 2015 Apr 7. PubMed PMID: 25912627. 3: Saito T, Katayama T, Sawada J, Kano K, Asanome A, Takahashi K, Sato N, Hasebe N. Combination therapy for segmental craniocervical dystonia (Meige syndrome) with aripiprazole, trihexyphenidyl, and botulinum toxin: three cases reports. Neurol Sci. 2015 Feb;36(2):243-5. doi: 10.1007/s10072-014-1927-x. Epub 2014 Aug 24. PubMed PMID: 25151364. 4: Maeda H, Tanaka R, Nakayama H. Inclusion complexes of trihexyphenidyl with natural and modified cyclodextrins. Springerplus. 2015 May 7;4:218. doi: 10.1186/s40064-015-0986-7. eCollection 2015. PubMed PMID: 26020020; PubMed Central PMCID: PMC4439407. 5: Shioya A, Tomidokoro Y, Ishii K, Ishii A, Tamaoka A. [Case report: a case of anterocollis ameliorated by trihexyphenidyl]. Nihon Naika Gakkai Zasshi. 2011 Nov 10;100(11):3325-8. Japanese. PubMed PMID: 22250425. 6: Robottom BJ, Reich SG. Exposure to high dosage trihexyphenidyl during pregnancy for treatment of generalized dystonia: case report and literature review. Neurologist. 2011 Nov;17(6):340-1. doi: 10.1097/NRL.0b013e31822b54d2. PubMed PMID: 22045287. 7: Petković S, Durendić-Brenesel M, Dolai M, Samojlik I. Fatal intoxication because of trihexyphenidyl. J Forensic Sci. 2011 Sep;56(5):1383-6. doi: 10.1111/j.1556-4029.2011.01816.x. Epub 2011 Jun 3. PubMed PMID: 21644988. 8: Zheng SQ, Wang W, Liang C, Wang R, Gong FJ, Wu ZP, Chen YS, Zhang YR, Zhang RS. [Simultaneous determination of trihexyphenidyl, chlorpromazine and clozapine in blood by GC-MS]. Fa Yi Xue Za Zhi. 2011 Aug;27(4):271-3. Chinese. PubMed PMID: 21913556. 9: Ben-Pazi H. Trihexyphenidyl improves motor function in children with dystonic cerebral palsy: a retrospective analysis. J Child Neurol. 2011 Jul;26(7):810-6. doi: 10.1177/0883073810392582. Epub 2011 Apr 15. PubMed PMID: 21498790. 10: Carranza-del Rio J, Clegg NJ, Moore A, Delgado MR. Use of trihexyphenidyl in children with cerebral palsy. Pediatr Neurol. 2011 Mar;44(3):202-6. doi: 10.1016/j.pediatrneurol.2010.09.008. PubMed PMID: 21310336. 11: De Rinaldis M, Gennaro L, Losito L, Trabacca A. Drug-to-drug interaction between sodium valproate and trihexyphenidyl in a child with extrapyramidal cerebral palsy and epilepsy. Eur J Clin Pharmacol. 2011 Mar;67(3):315-6. doi: 10.1007/s00228-010-0918-y. Epub 2010 Oct 20. PubMed PMID: 20959970. 12: Liu ZZ, Ji BS. The protective effect of trihexyphenidyl on the beta-amyloid peptide (25-35)-induced cytotoxicity in PC12 cells. Clin Exp Med. 2010 Dec;10(4):237-43. doi: 10.1007/s10238-010-0090-9. Epub 2010 Jan 26. PubMed PMID: 20101432. 13: Maccaroni E, Malpezzi L, Masciocchi N. Trihexyphenidyl hydro-chloride: a powder diffraction study. Acta Crystallogr Sect E Struct Rep Online. 2010 Sep 4;66(Pt 10):o2511. doi: 10.1107/S1600536810035294. PubMed PMID: 21587506; PubMed Central PMCID: PMC2983296. 14: Pomara N, Yi L, Belzer K, Facelle TM, Willoughby LM, Sidtis JJ. Retrograde facilitation of verbal memory by trihexyphenidyl in healthy elderly with and without the APOE epsilon4 allele. Eur Neuropsychopharmacol. 2010 Jul;20(7):467-72. doi: 10.1016/j.euroneuro.2010.03.004. Epub 2010 Apr 22. PubMed PMID: 20417063. 15: Wate SP, Borkar AA. Simultaneous spectrophotometric estimation of haloperidol and trihexyphenidyl in tablets. Indian J Pharm Sci. 2010 Mar;72(2):265-7. doi: 10.4103/0250-474X.65016. PubMed PMID: 20838539; PubMed Central PMCID: PMC2929794. 16: Gika AD, Hughes E, Goyal S, Sparkes M, Lin JP. Trihexyphenidyl for acute life-threatening episodes due to a dystonic movement disorder in Rett syndrome. Mov Disord. 2010 Feb 15;25(3):385-9. doi: 10.1002/mds.22926. PubMed PMID: 20063434. 17: Praharaj SK, Sarkhel S, Khanande RV, Sinha VK. Complete resolution of clozapine-induced sialorrhea with low dose trihexyphenidyl. Psychopharmacol Bull. 2010;43(4):73-5. PubMed PMID: 21240153. 18: Aggarwal A, Garg A, Jiloha RC. Trihexyphenidyl (benzhexol) in clozapine-induced nocturnal enuresis and sialorrhea. Indian J Med Sci. 2009 Oct;63(10):470-1. doi: 10.4103/0019-5359.57642. PubMed PMID: 19901488. 19: Rice J, Waugh MC. Pilot study on trihexyphenidyl in the treatment of dystonia in children with cerebral palsy. J Child Neurol. 2009 Feb;24(2):176-82. doi: 10.1177/0883073808322668. PubMed PMID: 19182155. 20: Appendino JP, Soman T. Correspondence on "Prospective open-label clinical trial of trihexyphenidyl in children with secondary dystonia due to cerebral palsy". J Child Neurol. 2008 Jul;23(7):846; author reply 846-7. doi: 10.1177/0883073808316369. PubMed PMID: 18658086.