Butolame | CAS#150748-23-5 | anticoagulant 17β-aminoestrogen

MedKoo Cat#: 145445 | Name: Butolame

Description:

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

Butolame is an anticoagulant 17β-aminoestrogen. Butolame is an anxiolytic for females with a hypoestrogenic condition. 17β-AEs may be a good alternative replacement therapy for women with symptoms associated with menopause.

Chemical Structure

Butolame

CAS#150748-23-5

Theoretical Analysis

MedKoo Cat#: 145445

Name: Butolame

CAS#: 150748-23-5

Chemical Formula: C22H33NO2

Exact Mass: 343.2500

Molecular Weight: 343.51

Elemental Analysis: C, 76.92; H, 9.68; N, 4.08; O, 9.31

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Buolame; Butolame;

IUPAC/Chemical Name

(8R,9S,13S,14S,17S)-17-((4-hydroxybutyl)amino)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-ol

InChi Key

AXFQQAQJYIXKGS-AANPDWTMSA-N

InChi Code

1S/C22H33NO2/c1-22-11-10-18-17-7-5-16(25)14-15(17)4-6-19(18)20(22)8-9-21(22)23-12-2-3-13-24/h5,7,14,18-21,23-25H,2-4,6,8-13H2,1H3/t18-,19-,20+,21+,22+/m1/s1

SMILES Code

[H][C@@]12CC[C@H](NCCCCO)[C@@]1(C)CC[C@]3([H])C4=CC=C(O)C=C4CC[C@@]23[H]

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 343.51 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.

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

1: Lemini C, García-Albor E, Cruz-López B, Matamoros-Trejo G, Martínez-Mota L. Differential effect of the 17β-aminoestrogens prolame, butolame and pentolame in anxiety and depression models in rats. Prog Neuropsychopharmacol Biol Psychiatry. 2016 Jan 4;64:102-8. doi: 10.1016/j.pnpbp.2015.07.013. Epub 2015 Jul 31. PMID: 26239795. 2: Lemini C, Rubio-Póo C, Silva G, García-Mondragón J, Zavala E, Mendoza-Patiño N, Castro D, Cruz-Almanza R, Mandoki JJ. Anticoagulant and estrogenic effects of two new 17 beta-aminoestrogens, butolame [17 beta-(4-hydroxy-1-butylamino)-1,3,5(10)-estratrien-3-ol] and pentolame [17 beta-(5-hydroxy-1-pentylamino)-1,3,5(10)-estratrien-3-ol]. Steroids. 1993 Oct;58(10):457-61. doi: 10.1016/0039-128x(93)90002-5. PMID: 8256254. 3: Lemini C, Canchola E. Induction of sexual behavior in female rats by the 17beta-aminoestrogens prolame, butolame and pentolame. Proc West Pharmacol Soc. 2009;52:39-42. PMID: 22128419. 4: Lemini C, Estela Avila M, Medina M, Sánchez C, Figueroa A, García-Mondragón MJ, Vargas-Vázquez A, Jiménez-Orozco A. Proliferative Properties of 17β-aminoestrogens in MCF-7 Human Breast Cancer Cells. Basic Clin Pharmacol Toxicol. 2017 Mar;120(3):235-242. doi: 10.1111/bcpt.12674. Epub 2016 Nov 30. PMID: 27638561. 5: Noriega L, Díaz A, Limón D, Castro ME, Caballero NA, Ramírez RE, Perez- Aguilar JM, Melendez FJ. Inhibitory mechanism of 17β-aminoestrogens in the formation of Aβ aggregates. J Mol Model. 2019 Jul 18;25(8):229. doi: 10.1007/s00894-019-4128-y. PMID: 31321557. 6: Jaimez R, Cooney A, Jackson K, Lemus AE, Lemini C, Cárdenas M, García R, Silva G, Larrea F. In vivo estrogen bioactivities and in vitro estrogen receptor binding and transcriptional activities of anticoagulant synthetic 17beta- aminoestrogens. J Steroid Biochem Mol Biol. 2000 May;73(1-2):59-66. doi: 10.1016/s0960-0760(00)00053-4. PMID: 10822025. 7: Flores-Soto E, Martínez-Villa I, Solís-Chagoyán H, Sommer B, Lemini C, Montaño LM. 17β-Aminoestrogens induce guinea pig airway smooth muscle hyperresponsiveness through L-type Ca(2+) channels activation. Steroids. 2015 Sep;101:64-70. doi: 10.1016/j.steroids.2015.06.001. Epub 2015 Jun 9. PMID: 26066899. 8: Segovia-Mendoza M, Mirzaei E, Prado-Garcia H, Miranda LD, Figueroa A, Lemini C. The Interplay of GPER1 with 17β-Aminoestrogens in the Regulation of the Proliferation of Cervical and Breast Cancer Cells: A Pharmacological Approach. Int J Environ Res Public Health. 2022 Sep 28;19(19):12361. doi: 10.3390/ijerph191912361. PMID: 36231664; PMCID: PMC9566056. 9: Rubio-Póo C, Lemini C, Silva G, García-Mondragón J, Zavala E, Castro D, Mendoza-Patiño N, Mandoki JJ. Comparison of the time course of anticoagulant and estrogenic effects of prolame, butolame, pentolame and hexolame, a homologous series of 17 beta-amino estrogens. Proc West Pharmacol Soc. 1993;36:143-7. PMID: 8378368. 10: Lemini C, Canchola E. Effects of 17beta-aminoestrogens on the sexual behavior of female rats. Physiol Behav. 2009 Mar 23;96(4-5):662-6. doi: 10.1016/j.physbeh.2009.01.003. PMID: 19385021. 11: Lemini C, Cruz-López B, Martínez-Mota L. Participation of estrogen receptors in the antidepressant-like effect of prolame on the forced swimming test. Pharmacol Biochem Behav. 2013 Jan;103(3):659-65. doi: 10.1016/j.pbb.2012.11.004. Epub 2012 Nov 13. PMID: 23159542. 12: Jayme V, Rubio C. Effect of chronic administration of two aminoestrogens (butolame and pentolame) on epididymal protein patterns of the rat. Proc West Pharmacol Soc. 2003;46:71-3. PMID: 14699890. 13: Jayme V, Rivera C, Rubio C. Comparative effect of chronic administration of two 17 beta-aminoestrogens, butolame and pentolame, on the reproductive system, fertility and progeny outcome of the male rat. Proc West Pharmacol Soc. 2003;46:68-70. PMID: 14699889. 14: Lemini C, Franco Y, Avila ME, Jaimez R. Estrogenic effects of 17 beta- aminoestrogens assessed in uteri of rats and mice. Eur J Pharmacol. 2005 Mar 14;510(3):235-9. doi: 10.1016/j.ejphar.2005.01.028. PMID: 15763248. 15: Lemini C, Franco Y, Avila ME, Jaimez R. Contrasting effects of estradiol and 17 beta-aminoestrogens on blood clotting time in rats and mice. Eur J Pharmacol. 2005 Mar 14;510(3):229-33. doi: 10.1016/j.ejphar.2005.01.027. PMID: 15763247. 16: Jaimez R, Rubio-Póo C, Lemini C. Effects on blood clotting time of 17 beta- estradiol and 17 beta-aminoestrogens in rats and mice. Proc West Pharmacol Soc. 2001;44:163-6. PMID: 11793970.