41:
593:
The FDA has recommended seizing any chemicals advertised as pangamic acid and restraining the importation and interstate shipment of pangamic acid on the grounds that pangamic acid and pangamic acid products are unsafe for use and have no known nutritional properties. Pangamic acid's distribution in
435:
seeds, and received the patent in 1949. A 1951 paper by the
Krebses reported the first isolation of this compound using this patented process, but did not include enough information to confirm that this compound was actually isolated. In 1955, the Krebses received a patent for another synthesizing
532:
Much of the clinical research on pangamic acid took place in the former Soviet Union, though that research often did not describe which of the many compounds called "pangamic acid" was used in the study. This research was also of limited quality due to being overwhelmingly
458:
Chemical compounds sold as "pangamic acid" for medicinal purposes have also had various chemical compositions, and suppliers of "pangamic acid" have regularly changed the identity of the chemical compounds sold under this label. One anecdote noted that the
447:' has been established in a scientifically verifiable manner to conform to the empiric formula" described by the Krebses. Analysis of a sample of a compound called "pangamic acid" which was provided by a co-worker of the Krebses in the 1950s showed only
475:
to stop sales. Afterwards, it was noted that GNC was still selling something in the same bottles with the same labels, likely a different compound. Due to ambiguity in situations like this, the FDA considers it "not an identifiable substance".
443:, and research into pangamic acid have focused on compounds of various chemical compositions. A review noted that of all the chemicals described in research about pangamic acid, "ot a single product labeled 'pangamate' or 'B
556:
as well as providing improvement in oxygen utilization, there is no significant evidence for any of these claims or that it is safe for human use. One review noted that it meets "the criteria that define a quack remedy".
354:, has no nutritional value, has no known use in the treatment of any disease, and has been called a "quack remedy". Although a number of compounds labelled "pangamic acid" have been studied or sold (including the 1951
436:
process for "N-substituted glycine esters of gluconic acid", but the patent contained no supporting data to confirm the process was able to synthesize compounds described by the patent, including pangamic acid.
713:
361:), no chemical compound, including those claimed by the Krebses to be pangamic acid, has been scientifically verified to have the characteristics that defined the original description of the compound.
759:
164:
727:
KREBS ET Sr; KREBS ET Jr; BEARD HH; MALIN R; HARRIS AT; BARTLETT CL (1951). "Pangamic acid sodium: A newly isolated crystalline water-soluble factor; a preliminary report".
517:, skin conditions, joint pain, and nerve pain, with none of these claims supported by evidence in the patent application. Early promotion for pangamic acid included use by
603:
854:
Herbert V, Gardner A, Colman N (June 1980). "Mutagenicity of dichloroacetate, an ingredient of some formulations of pangamic acid (trade-named "vitamin B15")".
248:
452:
693:
510:
819:
Gelernt MD, Herbert V (1982). "Mutagenicity of diisopropylamine dichloroacetate, the "active constituent" of vitamin B15 (pangamic acid)".
483:
d-gluconodimethylamino acetic acid (Krebes 1951), never synthesized. Alternative Soviet synthesis of calcium salt also fails to reproduce.
364:
The
Krebses derived the term "pangamic" to describe this compound which they asserted to be ubiquitous and highly concentrated in seeds (
439:
Subsequent attempts at synthesizing this ester by other researchers found Krebs' purported methods of producing pangamic acid were not
455:. Thus, "pangamic acid" is more a label used to describe one of any number of chemical compounds rather than a particular substance.
223:
346:, promoted it as a medicinal compound for use in treatment of a wide range of diseases. They also termed this chemical "vitamin B
232:
InChI=1S/C10H19NO8/c1-11(2)3-6(13)19-4-5(12)7(14)8(15)9(16)10(17)18/h5,7-9,12,14-16H,3-4H2,1-2H3,(H,17,18)/t5-,7-,8+,9-/m1/s1
889:
493:
Diisopropylamine dichloroacetate (Krebes 1955 patent "analogue"), synthesized. Readily hydrolyzes to known-toxic compounds.
917:
323:
460:
200:
573:
of compounds commonly found in preparations labelled "pangamic acid" including diisopropylamine dichloroacetate,
525:" by the Krebses, there is no evidence that it meets the definition of a vitamin as there is no evidence it is a
468:
932:
431:
for a process for extracting this chemical compound which they reported had been previously isolated from
927:
88:
62:
754:
708:
937:
130:
538:
676:
871:
836:
801:
736:
689:
647:
585:
suggests there may be concern for the development of cancer with the use of these substances.
497:
464:
40:
863:
828:
793:
639:
574:
271:
209:
140:
922:
578:
424:
890:"CPG Sec. 457.100 Pangamic Acid and Pangamic Acid Products Unsafe for Food and Drug Use"
544:
Although more recent claims include treatment of a wide variety of conditions including
343:
317:
471:(GNC), which agreed to stop selling the compound in those bottles after the FDA filed
911:
643:
553:
549:
487:
420:
342:, is the name given to a chemical compound discovered by Ernst T. Krebs Sr. His son,
189:
380:
Pangamic acid is the name given to the chemical compound with the empirical formula
566:
440:
51:-gluconodimethylamino acetic acid, a structure of "pangamic acid" proposed in 1951
594:
Canada has been prohibited by the then-named
Canadian Food and Drug Directorate.
518:
496:
Pharmacologically inert materials, ranging from "synthesis attempts" containing
832:
302:
867:
797:
479:
To summarize, substances that have been claimed to be pangamic acid include:
570:
534:
17:
740:
875:
840:
651:
805:
526:
490:. Result of attempts to synthesize the 1951 compound. Possibly mutagenic.
582:
472:
448:
432:
351:
176:
545:
514:
509:
The
Krebses' original patent claimed pangamic acid could be used for
428:
630:
Check WA (June 1980). "Vitamin B15--whatever it is, it won't help".
316:
Except where otherwise noted, data are given for materials in their
412:
163:
153:
729:
International Record of
Medicine and General Practice Clinics
711:, "Therapeutic material and method of obtaining the same"
784:
Herbert V (July 1979). "Pangamic acid ("vitamin B15")".
541:) and ignoring short and long term safety in human use.
411:
and a molecular weight of 281 which appeared to be an
757:, "N-substituted glycine esters of gluconic acid"
688:, New York: Churchill Livinstone, pp. 159–170],
521:
as well as humans. Although given the name "Vitamin B
675:
604:List of unproven and disproven cancer treatments
188:
581:, as well as dimethylglycine mixed with sodium
139:
669:
667:
665:
663:
661:
8:
892:. Food and Drug Administration. March 1995
29:
779:
777:
775:
773:
771:
769:
674:Herbert, Victor; Herbert, Robert (1981),
208:
625:
623:
621:
619:
615:
453:nuclear magnetic resonance spectroscopy
253:
228:
109:)-6--2,3,4,5-tetrahydroxyhexanoic acid
427:. In 1943, the Krebses applied for a
235:Key: ZQTHOIGMSJMBLM-BUJSFMDZSA-N
118:dimethylglycine d-gluconic acid ester
7:
179:
34:-gluconodimethylamino acetic acid
25:
359:-gluconodimethylamino acetic acid
644:10.1001/jama.1980.03300500005002
289:
283:
39:
486:Variety of mixtures containing
320:(at 25 °C , 100 kPa).
256:CN(C)CC(=O)OC((((C(=O)O)O)O)O)O
292:
277:
27:Hypothetical chemical compound
1:
505:Clinical claims and research
461:Food and Drug Administration
451:upon further evaluation by
350:", though it is not a true
954:
686:Controversies in nutrition
539:controlled experimentation
463:(FDA) has seized lots of "
833:10.1080/01635588109513714
537:in nature (as opposed to
314:
264:
244:
219:
123:
115:
87:
61:
56:
38:
513:as well as treatment of
469:General Nutrition Center
368:meaning "universal" and
868:10.1093/ajcn/33.6.1179
798:10.1093/ajcn/32.7.1534
677:"Pangamate ("Vitamin B
565:Positive results from
47:Chemical structure of
89:Systematic IUPAC name
918:Alternative medicine
529:needed by the body.
310: g·mol
78:-dimethylglycinyl)-
35:
638:(24): 2473, 2480.
344:Ernst T. Krebs Jr.
324:Infobox references
30:
856:Am. J. Clin. Nutr
786:Am. J. Clin. Nutr
695:978-0-443-08127-9
569:analysis via the
498:calcium gluconate
465:calcium pangamate
418:
372:meaning "seed").
358:
332:Chemical compound
330:
329:
165:Interactive image
81:
50:
33:
16:(Redirected from
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902:
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575:diisopropylamine
500:to pure lactose.
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410:
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272:Chemical formula
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79:
48:
43:
36:
31:
21:
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707:
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673:
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659:
629:
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612:
600:
591:
579:dichloroacetate
563:
524:
507:
446:
425:dimethylglycine
406:
403:
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401:
397:
394:
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28:
23:
22:
15:
12:
11:
5:
951:
949:
941:
940:
935:
930:
925:
920:
910:
909:
904:
903:
881:
862:(6): 1179–82.
846:
811:
792:(7): 1534–40.
765:
746:
719:
700:
694:
678:
657:
614:
613:
611:
608:
607:
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599:
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511:detoxification
506:
503:
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404:
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377:
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347:
338:, also called
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318:standard state
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136:
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92:
91:
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82:-gluconic acid
65:
59:
58:
54:
53:
45:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
950:
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936:
934:
933:Pseudoscience
931:
929:
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891:
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873:
869:
865:
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857:
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834:
830:
827:(3): 129–33.
826:
822:
815:
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803:
799:
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791:
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780:
778:
776:
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601:
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588:
586:
584:
580:
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568:
560:
558:
555:
554:schizophrenia
551:
550:heart disease
547:
542:
540:
536:
530:
528:
520:
516:
512:
504:
499:
495:
492:
489:
488:dimethylamine
485:
482:
481:
480:
477:
474:
470:
466:
462:
456:
454:
450:
442:
437:
434:
430:
426:
422:
421:gluconic acid
415:derived from
414:
375:
373:
371:
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360:
353:
345:
341:
337:
336:Pangamic acid
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100:
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64:
60:
55:
42:
37:
19:
928:Health fraud
894:. Retrieved
884:
859:
855:
849:
824:
820:
814:
789:
785:
749:
735:(1): 18–23.
732:
728:
722:
703:
685:
635:
631:
592:
589:Legal status
567:mutagenicity
564:
543:
531:
508:
478:
457:
441:reproducible
438:
379:
369:
365:
363:
355:
339:
335:
334:
124:Identifiers
116:Other names
106:
102:
98:
94:
75:
71:
67:
18:Vitamin B-15
938:Sugar acids
821:Nutr Cancer
519:race horses
265:Properties
912:Categories
896:25 October
755:US 2710876
709:US 2464240
610:References
467:" sold by
303:Molar mass
210:MPQ53A9F5C
152:3D model (
141:20858-86-0
131:CAS Number
63:IUPAC name
571:Ames test
535:anecdotal
376:Chemistry
340:pangamate
741:14840945
598:See also
527:nutrient
190:45934203
876:6992558
841:6752894
652:7382025
583:nitrite
449:lactose
433:apricot
352:vitamin
308:281.261
177:PubChem
923:Amines
874:
839:
806:377937
804:
761:
739:
715:
692:
650:
561:Safety
546:cancer
515:asthma
429:patent
249:SMILES
57:Names
413:ester
370:gamic
224:InChI
154:JSmol
898:2010
872:PMID
837:PMID
802:PMID
737:PMID
690:ISBN
648:PMID
632:JAMA
473:suit
423:and
201:UNII
864:doi
829:doi
794:doi
733:164
681:")"
640:doi
636:243
366:pan
180:CID
914::
870:.
860:33
858:.
835:.
823:.
800:.
790:32
788:.
768:^
731:.
684:,
679:15
660:^
646:.
634:.
618:^
577:,
552:,
548:,
523:15
445:15
396:19
387:10
348:15
287:19
281:10
105:,5
101:,4
97:,3
93:(2
70:-(
66:6-
900:.
878:.
866::
843:.
831::
825:3
808:.
796::
743:.
654:.
642::
419:-
417:d
409:N
405:8
400:O
391:H
382:C
357:d
296:8
293:O
290:N
284:H
278:C
156:)
107:R
103:R
99:S
95:R
80:D
76:N
74:,
72:N
68:O
49:d
32:d
20:)
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