(Rac)-5-Hydroxymethyl Tolterodine ((Rac)-Desfesoterodine) is an bioactive metabolite of Tolterodine and an mAChR antagonist (Kis for M1, M2, M3, M4, and M5 receptors are 2.3 nM, 2 nM, 2.5 nM, 2.8 nM and 2.9 nM). (Rac)-5-Hydroxymethyl Tolterodine may be used in overactive bladder research.

Physicochemical Properties

Molecular Formula	C22H31NO2
Molecular Weight	341.49
Exact Mass	341.235
CAS #	200801-70-3
Related CAS #	(Rac)-5-Hydroxymethyl Tolterodine-d14;1185071-13-9;5-Hydroxymethyl Tolterodine-d14 (formate)
PubChem CID	9927971
Appearance	White to off-white solid powder
Density	1.1±0.1 g/cm3
Boiling Point	490.7±45.0 °C at 760 mmHg
Flash Point	233.2±27.4 °C
Vapour Pressure	0.0±1.3 mmHg at 25°C
Index of Refraction	1.563
LogP	4.12
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	8
Heavy Atom Count	25
Complexity	357
Defined Atom Stereocenter Count	0
InChi Key	DUXZAXCGJSBGDW-UHFFFAOYSA-N
InChi Code	InChI=1S/C22H31NO2/c1-16(2)23(17(3)4)13-12-20(19-8-6-5-7-9-19)21-14-18(15-24)10-11-22(21)25/h5-11,14,16-17,20,24-25H,12-13,15H2,1-4H3
Chemical Name	2-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenol
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Ki: M1 (2.3 nM), M2 (2 nM), M3 (2.5 nM), M4 (2.8 nM), and M5 (2.9 nM)[1]
ln Vitro	The contraction of guinea-pig isolated urinary bladder strips caused by carbachol is competitively and concentration-dependently inhibited in vitro by (Rac)-5-Hydroxymethyl Tolterodine (PNU-200577) (KB of 0.84 nM; pA2 of 9.14)[2].
ln Vivo	Treatment with (Rac)-5-Hydroxymethyl Tolterodine (5-HMT; 0.88 μmol/kg; iv) demonstrates that the drug significantly binds to muscarinic receptors in all organs with the exception of the cerebral cortex, with the bladder exhibiting the longest duration of binding[3].
References	[1]. Antimuscarinic potency and bladder selectivity of PNU-200577, a major metabolite of tolterodine. Pharmacol Toxicol. 1997 Oct;81(4):169-72. [2]. The design and development of fesoterodine as a prodrug of 5-hydroxymethyl tolterodine (5-HMT), the active metabolite of tolterodine. Curr Med Chem. 2009;16(33):4481-9. [3]. Muscarinic receptor binding of fesoterodine, 5-hydroxymethyl tolterodine, and tolterodine in rat tissues after the oral, intravenous, or intravesical administration. J Pharmacol Sci. 2019 May;140(1):73-78.

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (292.83 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.32 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.32 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (7.32 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.9283 mL	14.6417 mL	29.2834 mL
	5 mM	0.5857 mL	2.9283 mL	5.8567 mL
	10 mM	0.2928 mL	1.4642 mL	2.9283 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.