chloropropanoylpretadalafil

updated

Chloropropanoylpretadalafil is a tadalafil-related compound with a chloropropanoyl modification, distinct from chloropretadalafil and tadalafil. FDA forensic chemists found it in a supplement sold for sexual enhancement. The only study isolated it and worked out its structure; nothing has tested whether it blocks PDE5, improves erections, how the body handles it or whether it is safe. Graded D for a characterized supplement ingredient whose clinical effects and safety are unmeasured; the grade does not mean it is safe.

Small-molecule tadalafil-related analog

  • The original paper isolated the compound from a sexual-enhancement supplement.
  • It is distinct from chloropretadalafil, nortadalafil, and tadalafil.
  • Chemical characterization is not clinical validation.

What did the researchers identify?

The researchers found a tadalafil-related compound with a chloropropanoyl modification and named it chloropropanoylpretadalafil. It differs from chloropretadalafil.

source: Kern et al., primary structural characterization, Kern SE, Lorenz LM, Lanzarotta A, Nickum EA, Litzau JJ. Isolation and structural characterization of a new tadalafil analog (chloropropanoylpretadalafil) found in a dietary supplement. Journal of pharmaceutical and biomedical analysis. 2016. DOI 10.1016/j.jpba.2016.05.038.

source: PubChem: chloropropanoylpretadalafil chemical identity, National Library of Medicine. PubChem CID 140466495.

What did the original investigation establish?

The investigators isolated a supplement constituent and characterized its chloropropanoyl modification using chromatography, spectroscopy and accurate mass. They did not test it as a treatment.

The correct primary record is PMID 27337189. Its reported protonated ion is m/z 441.1216; an ion formula should not be treated as the neutral molecule’s formula. The abstract supplies no functional PDE5 IC50, clinical PK or biological safety outcome.

source: Kern et al., primary structural characterization

What is known about human risk?

The study provides no clinical adverse-event profile, interaction data, human half-life or therapeutic dose. It also cannot tell whether the compound improves erectile function.

source: Kern et al., primary structural characterization

Why do some source links describe a different compound?

The cited PMC manuscript body describes chloropropanoylpretadalafil, but its header points to a different 2-hydroxyethylnortadalafil record. That is a bibliographic mismatch, not replication.

The manuscript describes a ten-capsule composite and coexisting analogs, with insufficient purity or quantity for definitive NMR work. Its header points to a different 2-hydroxyethylnortadalafil record, so it is not independent replication. The quantitative chloropropanoylpretadalafil result comes from PMID 27337189.

source: Kern et al., primary structural characterization

source: Author manuscript with bibliographic mismatch, Kern SE, Nickum EA, Flurer RA, Toomey VM, Litzau JJ. Isolation and structural characterization of a new tadalafil analog (2-hydroxyethylnortadalafil) found in a dietary supplement. Journal of pharmaceutical and biomedical analysis. 2015. DOI 10.1016/j.jpba.2014.10.021.

Studies and sources

Kern et al., primary structural characterization

Analytical identity or detection study

Kern SE, Lorenz LM, Lanzarotta A, Nickum EA, Litzau JJ. Isolation and structural characterization of a new tadalafil analog (chloropropanoylpretadalafil) found in a dietary supplement. Journal of pharmaceutical and biomedical analysis. 2016. DOI 10.1016/j.jpba.2016.05.038.

FDA forensic chemists isolated a supplement constituent and characterized its chloropropanoyl modification using HPLC-UV, GC/FTIR/MS and accurate mass. The reported ion is m/z 441.1216. This is a single-product chemical investigation, not an administered-human or animal efficacy experiment. No functional PDE5 IC50, clinical PK or biological safety outcome appears in the primary abstract.

Participants / model
A sexual-enhancement supplement sample
Follow-up
Analytical investigation
Study design
Primary chemical isolation and structural characterization
Read the original source
PubChem: chloropropanoylpretadalafil chemical identity

Government chemical identity database

National Library of Medicine. PubChem CID 140466495.

C23H21ClN2O5; molecular weight 440.9 g/mol.

Participants / model
Chemical record
Follow-up
Living database
Study design
Curated structure record

Formula and molecular weight establish the recorded structure, not the contents of a retail product or an effective dose.

Read the original source
Author manuscript with bibliographic mismatch

Author manuscript

Kern SE, Nickum EA, Flurer RA, Toomey VM, Litzau JJ. Isolation and structural characterization of a new tadalafil analog (2-hydroxyethylnortadalafil) found in a dietary supplement. Journal of pharmaceutical and biomedical analysis. 2015. DOI 10.1016/j.jpba.2014.10.021.

The manuscript body describes chloropropanoylpretadalafil in a composite of ten capsules, with coexisting nortadalafil and N-ethyltadalafil and too little purity or material for definitive NMR elucidation. It points to a 2002 patent intermediate. Its header, PMID 25462127 and DOI 10.1016/j.jpba.2014.10.021, identifies a different 2-hydroxyethylnortadalafil paper. This mismatched record is not independent replication; the quantitative chloropropanoylpretadalafil result comes from PMID 27337189.

The manuscript introduction and methods do not match its bibliographic header.

Read the original source

Why is chloropropanoylpretadalafil in D tier?

D: a characterized supplement ingredient with unmeasured clinical effects and safety. The grade describes missing biological evidence; it does not establish safety or superiority to the other analogs.

how tiers are graded: methodology · every cited source · about reptides.

Research reference, not medical advice. Entries distinguish product labels, study doses and reported protocols. Check the linked source for the product, route and population.