Old English toðleas, in the literal sense; see tooth + -less. Figurative sense of "dull" is recorded from 1590s; that of "lacking enforcement powers" is first recorded 1961. Related: Toothlessly; toothlessness.
Old English toð (plural teð), from Proto-Germanic *tanthu- (source also of Old Saxon, Danish, Swedish, Dutch tand, Old Norse tönn, Old Frisian toth, Old High German zand, German Zahn, Gothic tunþus), from PIE root *dent- "tooth." Plural teeth is an instance of i-mutation.
The loss of -n- before spirants is regular in Old English, Old Frisian, and Old Saxon: compare goose (n.), five, mouth (n.). Also thought, from stem of think; couth from the stem of can (v.1); us from *uns.
Application to tooth-like parts of other objects (saws, combs, etc.) first recorded 1520s. Tooth and nail as weapons is from 1530s. The tooth-fairy is attested from 1964.
word-forming element meaning "lacking, cannot be, does not," from Old English -leas, from leas "free (from), devoid (of), false, feigned," from Proto-Germanic *lausaz (cognates: Dutch -loos, German -los "-less," Old Norse lauss "loose, free, vacant, dissolute," Middle Dutch los, German los "loose, free," Gothic laus "empty, vain"), from PIE root *leu- "to loosen, divide, cut apart." Related to loose and lease.
<a href="https://www.etymonline.com/word/toothless">Etymology of toothless by etymonline</a>
Harper, D. (n.d.). Etymology of toothless. Online Etymology Dictionary. Retrieved $(datetime), from https://www.etymonline.com/word/toothless